Regis Technologies Chiral Application Guide Chiral Application Guide 6 VOLUME
Regis Technologies
ChiralApplicationGuide
ChiralApplicationGuide
6V O L U M E
DURABLE, HIGH EFFICIENCY CHIRAL COLUMNS
Since 1980, Regis Technologies, Inc. has proven to be a leader inchiral separations and services. Our support system to the
analytical and preparative chromatographer is a model othermanufacturers of chiral products try to emulate. Our technicalexpertise, professional staff, and worldwide distribution network ishighly respected and praised in the chiral community.
Regis offers four different types of Chiral StationaryPhases (CSP’s):• Covalently bonded Pirkle-Type Concept • Protein-based • Covalently bonded 18 Crown-ether
The complete line of Pirkle-Type CSP’s aremanufactured on-site at our cGMP facility inMorton Grove, Illinois. Columns range fromanalytical to preparative in size. Since Regispacks their own columns, custom sized columns areeasily attainable.
Regis maintains an extended inventory of Protein-based columnsmanufactured by ChromTech in the United Kingdom and thecovalently bonded 18 Crown-Ether columns manufactured by RStechin South Korea. Information on these product lines is readilyavailable on our website at www.registech.com.
As evidence of our commitment to the scientist in the lab, Regis ispleased to present its Chiral Application Guide VI. This new guidecontains over 500 specific chiral applications using a variety ofchiral column types. We have also included a few new sections inthis guide. We added a Frequently Asked Question section and aQuick Scheme Method Development section.
For applications not listed in this guide, Regis maintains a dedicatedchiral separations lab and chiral separations scientist. This enablesRegis to offer a Free Chiral Screening Service to the scientificcommunity. For specific column types, services or applications notlisted in this guide, please contact Regis directly or visit our websitefor continuously updated information.
Regis Technologies, Inc.
All Regis Chiral
Separations
products must
meet rigorous
manufacturing and
quality control
specifications
before release.
1
2
Advantages of the Pirkle-Type Chiral Stationary Phases 3
Introduction to Regis Chiral Stationary Phases 4Pirkle Chiral Stationary PhasesProtein-based Chiral Stationary Phases RStech Corporation ChiroSil® RCA(+) and SCA(-)
18 Crown-Ether Chiral Stationary Phases
Regis HPLC Chiral Column Product List 7
Aryl Propionic Acid Non Steroidal Anti-Inflammatory Drugs (NSAIDS) 8
Other Carboxylic Acids 11
Basic Nitrogen 15
Basic Amine 15
Esters, Lactones, Ketones, Anhydrides 16
Amides, Imides, Carbamates, etc. 20
Epoxides 24
Alcohols 25
Diols, Hydroxyketones, etc. 32
Sulfoxides 33
Phosphorous Compounds 36
Atropisomers 39
Optical Switches, Liquid Crystal Components 47
Allenes 48
Organometallic Compounds 53
Agricultural Compounds 56
Miscellaneous Pharmaceuticals 61
Barbiturates, Ureas and Diol Epoxides 74
Natural Products 75
β-Blockers 76
Amino Acids 79
Frequently Asked Questions 82
Quick Scheme Method Development 83
References 86
Index 87Applications by CompoundApplications by Column Type
Chiral Screening Data Sheet 91
C O N T E N T S
CHIRAL HPLC APPLICATION GUIDE VI
Regis Technologies, Inc.3
Advantages of the Pirkle-Type Chiral Stationary Phases
Universal Solvent CapabilityThe entire family of Regis’ Pirkle-Type Chiral Stationary Phases (CSP’s) canbe used in BOTH normal and reversed-phase solvents. Due to the fact that allof the Pirkle-Type CSP’s are covalently bonded, the columns can tolerate allcommonly used mobile phase combinations.
Column DurabilityAnother advantage of covalent bonding is column durability. Listed beloware a few distinct benefits associated with the Pirkle-Type CSP’s:• Long lasting columns• Bonded selector will not leach off the silica gel• Can tolerate sample overload• Can utilize strong solvents for cleaning• Columns are fully reversible• Compatible in SFC and SMB applications
Ability to Invert Elution OrderAll of the Pirkle-Type CSP’s are available in both enantiomeric forms. Thisallows the Chromatographer to invert the elution order of the enantiomers bysimply switching columns. This advantage is essential when determiningenantiomeric purity when the trace enantiomer should elute before the major.Elution order is also important in preparative chromatography because whenthe desired enantiomer elutes first, purity and production efficiencyincreases.
Chromatographic EfficiencyUnlike most Chiral columns on the market, Pirkle-Type Chiral HPLC columnsshow excellent chromatographic efficiency. The high density of binding sitesallows larger amounts of sample to be injected without major changes incolumn performance.
Ease of Scale-upPirkle-Type CSP’s were designed to allow the Chromatographer to scale-uptheir separation from analytical to preparative in a linear fashion. Regis usesthe highest grade silica gels available on the market today. The 5-micronCSP’s are bonded on Exsil®. Our 10-micron and 16-micron CSP’s arebonded on Kromasil®. Synthesis of the chiral selectors, bonding of thedifferent CSP’s, and column production is all performed by Regis in onefacility. This allows Regis total control over the product line. This also allowsRegis to perform special requests for the customer, including custom bondingand custom column packing.
REGIS Introduct ion to Regis Chiral Stat ionary Phases
Pirkle Chiral Stationary Phases
The Pirkle-Concept Chiral Stationary Phases generally fall into three classes: π-electronacceptor/π-electron donors, the π-electron acceptors and the π-electron donors. WithPirkle Phases, chiral recognition occurs at binding sites. Major binding sites areclassified as π-basic or π-acidic aromatic rings, acidic sites, basic sites, and stericinteraction sites. Aromatic rings are potential sites for π-π interactions. Acidic sitessupply hydrogens for potential intermolecular hydrogen bonds-the hydrogen is often anamido proton (N-H) from an amide, carbamate, urea, or amine. Basic sites, such as π-electrons, sulfinyl or phosphinyl oxygens, and hydroxy or ether oxygens, may also beinvolved in hydrogen bond formation. Steric interactions may also occur between largegroups.
π-Electron Acceptor/π-Electron Donor Phases
• WHELK-O 1• WHELK-O 2• ULMO
The latest and most revolutionary addition to the Pirkle-Concept series is the π-electronacceptor/π-electron donor phase. This concept is an innovative incorporation of bothπ-acceptor and π-donor characteristics, resulting in a phase that can be used for a widevariety of compound groups.
WHELK-O 1The Whelk-O 1 Chiral Stationary Phase is based on 1-(3,5-Dinitrobenzamido)-1,2,3,4,-tetrahydrophenanthrene. This phase allows separation of underivatizedracemates from a number of families including amides, epoxides, esters, ureas,carbamates, ethers, aziridines, phosphonates, aldehydes, ketones, carboxylic acids,and alcohols.
The Whelk-O 1 was originally designed for the separation of underivatized non-steroidal anti-inflammatory drugs (NSAIDs). This π-electron acceptor/π-electron donorphase exhibits an extraordinary degree of generality, allowing resolution of a widevariety of underivatized racemates. This broad versatility observed on the Whelk-O 1column, compares favorably with polysaccharide-derived chiral stationary phases. Inaddition, because of the Whelk-O 1’s covalent nature, this chiral phase is compatiblewith all commonly used mobile phases, including aqueous systems-a distinct advantageover polysaccharide-derived chiral stationary phases. Other advantages includecolumn durability, excellent efficiency, elution order inversion allowing availability ofboth enantiomeric forms, and excellent preparative capacity.
4 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
less stableadsorbate
(S,S)(S,S)(S)
(R)
a) Schematic diagram showing keyfunctional groups of the Whelk-O 1 involved in chiral recognition.
b) Schematic diagram showinggeneralized structure of analytes whichare resolved on the Whelk-O 1.
a) b)
more stableadsorbate
DNB
H-bond donor
H-bond acceptorTetrahydro-phenanthreneπ system
Dinitrobenzamideπ-system
Conjugated π-system
Whelk-O 1
WHELK-O 2The Whelk-O 2 is the covalent trifunctional version of the Whelk-O 1. The Whelk-O 2retains the same chiral selector but modifies the support to silica from a monofunctionallinkage to a trifunctional. In most cases, the enantioselectivity remains the sameallowing the separation of the analogous family of racemates as does the Whelk-O 1.
Whelk-O 2 was designed to enhance the stability of the stationary phase due to hydrolysis while using strong organic modifiers such as trifluoroacetic acid. TheWhelk-O 2 is ideal for preparative separations since the material is bonded on 10 µm100 Å spherical Kromasil silica. This allows the preparative chromatographer toperform method development on their analytical column and immediately scale-up tolarger diameter columns.
ULMOThe ULMO chiral stationary phase was developed by Austrian Researchers, Uray,Lindner, and Maier. This CSP has a general ability to separate the enantiomers of manyracemate classes, and is particularly good at separating the enantiomers of arylcarbinols.
The ULMO CSP is based on a 3,5-Dinitrobenzoyl derivative of diphenylethylene-diamine.
π-Electron Acceptor Phases
• DACH-DNB• Pirkle 1-J• α-Burke 2• β-Gem 1• Leucine• Phenylglycine
The π-electron acceptor Pirkle Chiral Stationary Phases can be used to separate a widerange of enantiomers without derivatization, as demonstrated for the following classesof solutes: secondary benzyl alcohols, mandelic acid analogs, α-hydroxy-α-aryl phosphates, α-tetralol analogs, propranolol analogs, β-hydroxy-aryl sulfoxides,alkyl-aryl sulfoxides, diaryl sulfoxides, aryl-substituted cyclic phthalides, aryl-substitutedlactams, aryl-substituted succinimides, aryl-substituted hydantoins, bi-β-naphthol and itsanalogs, and α-aryl acetamides.
DACH-DNBThe innovative DACH-DNB CSP was designed by Italian chemists Dr. FrancescoGasparrini, Misiti and Villani at Rome University “La Sapienza.” The DACH-DNB CSP;which contains the 3,5-dinitrobenzoyl derivative of 1,2-diaminocyclohexane, has beenfound to resolve a broad range of racemate classes including amides, alcohols, esters,ketones, acids, sulfoxides, phosphine oxides, selenoxides, phosponates,thiophosphineoxides, phosphineselenides, phosphine-boranes, β-lactams, organo-metallics, atropisomers and heterocycles.
PIRKLE 1-JThe Pirkle 1-J CSP is based on 3-(3,5-Dinitrobenzamido)-4-pheny-β-lactam. This unusualβ-lactam structure significantly alters its molecular recognition properties. The Pirkle 1Jis useful for the direct separation of underivatized β-blocker enantiomers. It can alsobe used for the separation of the enantiomers of arylpropionic acid NSAID’s as wellas other drugs.
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 5
Whelk-O 2
ULMO
DACH-DNB
Pirkle 1-J
Introduct ion to Regis Chiral Stat ionary Phases REGIS
REGIS Introduct ion to Regis Chiral Stat ionary Phases
α-BURKE 2The α-Burke 2 phase, first prepared by J. A. Burke III, a graduate student of Dr. Pirkle, isderived from dimethyl N-3,5-dinitro-benzoyl-α-amino-2,2-dimethyl-4-pentenylphosphonate. The α-Burke 2 has been specifically designed to directly separate theenantiomers of β-blockers without chemical derivatization, but this chiral phase is notlimited solely to the separation of β-blocker enantiomers. It also resolves the enantiomersof many compounds separated on π-acceptor Pirkle type chiral stationary phases.
β-GEM 1β-Gem 1 is a π-acceptor chiral stationary phase and is derived from N-3,5-dinitrobenzoyl-3-amino-3-phenyl-2-(1,1-dimethylethyl)-propanoate.
For a great many analytes, this chiral phase considerably outperforms its widely usedanalog, phenylglycine. It can separate anilide derivatives of a wide variety of chiralcarboxylic acids, including nonsteroidal anti-inflammatory agents.
LEUCINEThe leucine CSP is based on the 3,5-dinitrobenzoyl derivative of leucine. This π-acceptorphase demonstrates enhanced enantioselectivities for several classes of compounds,including benzodiazapines.
PHENYLGLYCINEPhenylglycine is based on the 3,5-dinitrobenzoyl derivative of phenylglycine.
This CSP resolves a wide variety of compounds which contain π-basic groups. Theseinclude: aryl-substituted cyclic sulfoxides, bi-β-naphthol and its analogs, α-indanol and α-tetralol analogs, and aryl-substituted hydantoins.
Protein-Based Chiral Stationary Phases
Regis Technologies carries a line of protein-based chiral columns manufactured byChromTech AB, United Kingdom. For additional product information and a Protein-BasedChiral Stationary Phase application guide, please contact Regis directly.• Chiral AGP (α-glycoprotein)• Chiral CBH (cellobiohydrolase)• Chiral HSA (human serum albumin)
RStech Corporation ChiroSil® RCA(+) and SCA(-) 18Crown-Ether Chiral Stationary Phases• ChiroSil RCA(+)• ChiroSil SCA (-)
Developed by RStech Corporation in Daejeon, Korea, the ChiroSil phase is the newestaddition to our chiral line of columns. This phase is prepared by a covalent trifunctionalbonding of (+) or (-)-(18-Crown-6)-tetracarboxylic acid as the chiral selector.
This phase which is available in analytical as well as preparative columns, is an excellentchoice for the separation of amino acids and compounds containing primary amines.
Like our other line of columns, this phase is highly durable, has universal solventcompatibility, and has the ability to invert elution order.
As described above, Regis’ Chiral columns can be used to separate a wide variety ofenantiomers in numerous compound groups. Please refer to the Product List on page 7for particular column types, sizes, configurations and product numbers. Consult theapplication separation data section that begins on page 8 for information regardingspecific chiral separations on a wide variety of compounds. See Application Indexes onpage 87.
6 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Phenylglycine
Leucine
ChiroSil
β-Gem 1
α-Burke 2
Regis Chiral Column Product Lis t REGIS
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 7
PRODUCT PARTICLE SIZE COLUMN DIMENSIONS PRODUCT#
(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm 786201(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm 786202(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm 786205(S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm 786101(S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm 786102(S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm 786105
(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm 786515(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm 786525(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1 mm 786535(R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm 786545(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm 786708(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm 786709(R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm 786713(R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm 786710(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm 786615(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm 786625(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1mm 786635(S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm 786645(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm 786702(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm 786703(S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm 786716(S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm 786704
(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm 786315(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm 786325(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1 mm 786335(R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm 786345(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm 786727(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm 786728(R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm 786732(R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm 786729(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm 786415(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm 786425(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1mm 786435(S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm 786445(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm 786721(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm 786722(S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm 786736(S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm 786723
(R,R)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm 787200(R,R)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm 787201(R,R)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm 787203(S,S)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm 787100(S,S)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm 787101(S,S)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm 787103
(R,R)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm 787202(R,R)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm 787707(R,R)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm 787708(R,R)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm 787712(R,R)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm 787709(S,S)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm 787102(S,S)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm 787701(S,S)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm 787702(S,S)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm 787715(S,S)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm 787703
PRODUCT PARTICLE SIZE COLUMN DIMENSIONS PRODUCT#
(R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm 788101(R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm 788102(R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm 788104(S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm 788201(S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm 788202(S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm 788204
(R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm 788103(R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm 788707(R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm 788708(R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm 788712(R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm 788709(S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm 788203(S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm 788701(S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm 788702(S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm 788715(S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm 788705
(3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm 731044(3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm 731244(3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm 731045(3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm 731245
(R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm 735035(R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm 735235(S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm 735037(S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm 735237
(R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm 731043(R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm 731243(S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm 731029(S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm 731229
D-Leucine 5 µm, 100 Å 25 cm x 4.6 mm 731054D-Leucine 5 µm, 100 Å 25 cm x 10.0 mm 731254L-Leucine 5 µm, 100 Å 25 cm x 4.6 mm 731041L-Leucine 5 µm, 100 Å 25 cm x 10.0 mm 731241
D-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm 731021D-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm 731221L-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm 731024L-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm 731224
Chiral AGP 5 µm, 300 Å 10 cm x 4.0 mm 732200Chiral AGP 5 µm, 300 Å 15 cm x 4.0 mm 732199Chiral CBH 5 µm, 300 Å 10 cm x 4.0 mm 732350Chiral CBH 5 µm, 300 Å 15 cm x 4.0 mm 732351Chiral HSA 5 µm, 300 Å 10 cm x 4.0 mm 732240Chiral HSA 5 µm, 300 Å 15 cm x 4.0 mm 732239
ChiroSil® RCA(+) 5 µm, 100 Å 15 cm x 4.6 mm 799001ChiroSil® RCA(+) 5 µm, 100 Å 25 cm x 4.6 mm 799002ChiroSil® SCA(-) 5 µm, 100 Å 15 cm x 4.6 mm 799101ChiroSil® SCA(-) 5 µm, 100 Å 25 cm x 4.6 mm 799102
Bulk material is available for all Chiral Stationary Phases
For column dimensions not listed, please contact Regis
NOTE: All columns (except the protein-based columns) listed contain chiral stationary phases that are covalently bound on 5 µm or 10 µm 100 Åspherical silica. A large variety of column dimensions and/or particle sizes are available upon request.
REGIS Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs)
8 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Ketoprofen Naproxen (semi prep)
Cicloprofen
Etodolac
Tiaprofenic Acid
Fenoprofen
Ketoprofen as 1-naphthylamidePirprofen
KetoprofenColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (47/47/6)
CH2Cl2/Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.63α = 1.35reference 46
CH3
OH
OO
H3C
Naproxen (semi prep on analytical column)
80:20:0.5 hexane/IPA/HOAc1 ml/min; 300 nmRun Time = 18 mininject 400 µl @
31.5 mg/ml = 12.6 mg4.6 mm x 25 cm Whelk-O 1reference 6
FenoprofenColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (98/2)
Hexane/IPA +0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14.5 mink'1 = 2.62α = 1.66reference 46
EtodolacColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98/2)
Hexane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14.5 mink'1 = 2.43α = 1.50reference 48
Cicloprofen20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.16α = 2.15reference 4
CH3
OH
O
Tiaprofenic Acid20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.02α = 1.09reference 4
CH3
OH
O
SO
CH3
OH
ON
Cl
Pirprofen20% IPA/hex, 1g/LNH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.85α = 1.81reference 4
Column: (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (70/30)
Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 230 nmRun Time = 13 mink'1 = 1.51α = 1.25reference 48
Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) REGISNaproxen (R:S=30:70) Cicloprofen
Naproxen (Normal Phase)
Naproxen (Reversed Phase)
Flurbiprofen
Ibuprofen
Naproxen Diisopropyl AmideLoxoprofen
Column = (S,S)-ULMO25 cm x 4.6 mmMobile Phase (90/10)
Heptane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 230 nmRun Time = 8.5 mink'1 = 1.54α = 1.34reference 48
CH3
OH
O
Cicloprofen70:30:0.5 hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.48α = 1.35reference 26
IbuprofenColumn = (R,R)-Whelko-O 1
25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/IPA +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.8 mink'1 = 3.21α = 1.72reference 46
FlurbiprofenColumn = (R,R)-Whelko-O 1
25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/IPA +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 20.5 mink'1 = 5.90α = 1.76reference 46
Naproxen (Reversed Phase)Column = (R,R)-Whelko-O 1
25 cm x 4.6 mmMobile Phase: (80/20)
CH3OH/H2O + 0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 1.63α = 1.64reference 46
Naproxen (Normal Phase)Column = (R,R)-Whelko-O 1
25 cm x 4.6 mmMobile Phase: (60/40)
Hexane/IPA + 0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 1.40α = 2.03reference 46
Naproxen Diisopropyl Amide10%EtOH/hex1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.23α = 1.53reference 26
LoxoprofenColumn = (R,R)-Whelko-O 1
25 cm x 4.6 mmMobile Phase: (85/15)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 15.0 mink'1 = 5.41α = 1.30reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 9
H3CO
CH3
N
O
REGIS Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs)
3,5-Dimethylanilide-R,S-Ibuprofen Naproxen Methyl Ester
Naproxen
Indoprofen
α-Trityl-2-naphthalene Propionic Acid
Naproxen Methyl Amide
Column = (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase = (85/15)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 13.0 mink'1 = 2.91α = 1.36reference 46
H3CO
CH3
OCH3
O
Naproxen Methyl Ester20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.42α = 1.42reference 14
H3CO
CH3
N
O
CH3
H
Naproxen Methyl Amide20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 18.73α = 1.41reference 14
IndoprofenColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (80/20)
Hexane/Ethanol + 0.01 M Ammonium Acetate
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time 17.0 mink'1 = 8.93α = 1.32reference 46
Rebamipide2-(4-Hydroxy-Phenoxy) Propionic Acid2-(4-Hydroxy-Phenoxy)
Propionic AcidColumn = (R,R)-ULMO
25 cm x 4.6 mmMobile Phase: (97/3)
Hexane/Ethanol+ 0.1% TFA
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 22.5 mink'1 = 9.02α = 1.27reference 46
RebamipideColumn = (S,S)-Whelk-O 2
10/100 25 cm x 4.6 mmMobile Phase: (85/15)
Hexane/Ethanol+ 0.1% TFA
Flow Rate = 2.0 mL/minDetection = UV 220 nmk'1 = 9.64α = 1.21reference 46
NaproxenExtract from Aleve® tablet (99.4%ee)80:20:0.5 hexane/IPA/HOAc2 ml/min; 254 nmRun Time = 10 min4.6 mm x 25 cm (S,S)
Whelk-O 1Sample prep: 1/2 tablet partitioned
between 1M HC1 (2 ml) andCH2C12 (5 ml) with sonication.CH2C12 layer filtered through glasswool and injected
α-Trityl-2-naphthalene propionic acid
Column = (R,R)-ULMO25 cm x 4.6 mm
Mobile Phase =(97/3)Hexane/IPA
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 1.57α = 1.79reference 46
CH3
OH
O
O
H3C
10 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Hydratropic Acid CarprofenHydratropic AcidColumn = (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase: (98/2)Hexane/IPA+ 0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 1.89α = 1.34reference 46
CarprofenColumn = (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase: (85/15)
Hexane/IPA+ 0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 4.70α = 1.73reference 46
Other Carboxyl ic Acids REGISTetrahydropyrimindine Carboxylic Acid Phenylbutyric acid
Column: (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (90/10)
Heptane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 215 nmRun Time: 14 mink'1 = 3.38α = 1.21reference 48
Column = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPA + 0.1% TFAFlow Rate = 2.0 mL/minDetection = UV 215 nmRun Time = 6.5 mink'1 = 3.19α = 1.16reference 48
OH
O
99:1:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 17 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.06α = 1.28reference 18
99:1:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 16 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.45α = 1.38reference 18
k'1 = 3.45
1 38
OH
O
Ph PhPh
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 11
Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) REGIS
REGIS Other Carboxyl ic Acids
2-Phenylcyclopropane Carboxylate Trolox
1,1'-binaphthyl-2,2'-diylhydrogen phosphateMandelic Acid
OCH3
OOH
CH3
CH3
H3C
HO
Trolox95:5:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 19 min4.6 mm x 25 cm
Whelk-O 1k'1 = 5.09α = 1.21reference 18
OH
O
2-Phenylcyclopropane Carboxylate
99:1 hexane/IPA1 ml/min; 220 nmRun Time = 18 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.19α = 1.34reference 18
56:44 H2O/MeOH, 0.1%HOAc1 ml/min; 254 nmRun Time = 18 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.46α = 1.27
OH
OH
O
Mandelic Acid0.1% HOAc in water1 ml/min; 254 nmRun Time = 13 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.08α = 1.13reference 18
O
O
P
OH
O
Trolox Calcium Channel Blocker
O
CH3
OH
O
CH3
HO
H3C
CH3
Column = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA +0.1% Acetic acid
Flow Rate = 1.5 mL/minDetection = UV 280 nmRun Time = 12.5 mink'1 = 2.18α = 2.68reference 46
Column = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 230 nmRun Time = 6 mink'1 = 0.55α = 2.06reference 48
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA + 0.1%Trifluoroacetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 2.03α = 2.10reference 49
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA + 0.1%Trifluoroacetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 4.20α = 1.11reference 50
12 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Other Carboxyl ic Acids REGIS
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 13
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA + 0.1%Trifluoroacetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 14.5 mink'1 = 7.24α = 1.22reference 50
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA + 0.1%Trifluoroacetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 2.07α = 2.62reference 49
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA + 0.1%Trifluoroacetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 11.5 mink'1 = 5.44α = 1.34reference 50
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (95/5)
Hexane/IPA + 0.1%Trifluoroacetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 3.5 mink'1 = 0.84α = 1.36reference 49
Phenylsuccinic Acid 4-Chloromandelic Acid
Ketorolacα-Methoxyphenyl Acetic Acid
Phenylsuccinic AcidColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 1.71α = 1.22reference 48
4-Chloromandelic AcidColumn = (R,R)-Whelk-O 2
25 cm x 4.6 mmMobile Phase = (70/30)
H2O/CH3OH+ 0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 1.95α = 1.43reference 46
α-Methoxyphenyl Acetic AcidColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (90/10)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 220 nmRun Time = 10.0 mink'1 = 2.96α = 1.61reference 46
KetorolacColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (98/2)
Hexane/IPA + 0.1% TFA
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 20.0 mink'1 = 8.87α = 1.15reference 46
Suprofen Ditoluoyltartaric Acid
1-Cyclopentyl-1-phenylacetic AcidTrolox-methylether
Ditoluoyltartaric AcidColumn: (S,S)-ULMO
25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 12.0 mink'1 = 2.47α = 1.19reference 48
SuprofenColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (80/20) Hexane/IPA +0.01 M Ammonium Acetate
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 18.0 mink'1 = 9.76α = 1.27reference 46
1-Cyclopentyl-1-phenylacetic AcidColumn: (S,S)-ULMO 25 cm
x 4.6 mmMobile Phase: (99/1)
Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 12.0 mink'1 = 2.46α = 1.19reference 48
Trolox-methyletherColumn: (S,S)-ULMO
25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 6.0 mink'1 = 0.32α = 2.50reference 48
14 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Other Carboxyl ic Acids
1-Cyclohexyl-1-phenylacetic Acid 2-(2-Chloro-4-methylphenoxy)propionic Acid
2-(3-Chlorophenoxy) Propionic AcidVanilmandelic Acid
1-Cyclohexyl-1-phenylacetic AcidColumn: (S,S)-ULMO 25 cm
x 4.6 mmMobile Phase: (99/1)
Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 13.0 mink'1 = 2.53α = 1.18reference 48
2-(2-Chloro-4-methylphenoxy)propionic AcidColumn: (S,S)-ULMO 25 cm x 4.6 mmMobile Phase: (99/1)
Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 11.0 mink'1 = 2.22α = 1.11reference 48
Vanilmandelic AcidColumn: (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6Moblie Phase: (85/15)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate: 2.0 mL/minDetection: UV 254 nmRun Time: 22.0 mink'1 = 12.34α = 1.27reference 46
2-(3-Chlorophenoxy) Propionic AcidColumn: (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6Moblie Phase: (99/1)
Hexane/IPAFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 17.0 mink'1 = 6.09α = 1.42reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 15
Other Carboxyl ic Acids REGIS4-(Trifluoromethyl)mandelic Acid 2,3-Dibenzoyl-Tartaric Acid
2,3-Dibenzoyl-Tartaric AcidColumn: (R,R)-ULMO
10/100 25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/Ethanol + 10 mM Ammonium Acetate
Flow Rate: 1.5 mL/minDetection: UV 254 nmk'1 = 4.87α = 1.33reference 46
4-(Trifluoromethyl)mandelic AcidColumn: (S,S)-Whelk-O 1
25 cm x 4.6Moblie Phase: (92/8)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 11.0 mink'1 = 3.59α = 1.40reference 46
Troger’s BaseColumn: (R,R)-Whelk-O 1
(10/100) (FEC) 25 cm x 4.6 mmMobile Phase: (96/4) Hexane/EthanolFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time = 10.0 mink'1 = 2.52α = 1.80reference 46
N
N
O
Bz
CH3
30% EtOH/hexane1 ml/min; 254 nmrun time = 18 min4.6 mm x 25 cm
Whelk-O 1k'1 = 2.46α = 2.09reference 18
Basic Nitrogen REGIS Basic Amine REGIStrans-11,12-Diamino-9,10-dihydro-9,10-ethanoanthracenetrans-11,12-Diamino-9,10-
dihydro-9,10-ethanoanthraceneColumn = ChiroSil® RCA(+)
15 cm x 4.6 mmMobile Phase = (80/20)
CH2OH/H2O+ 0.1% Phosphoric acid
Flow Rate = 1.0 mL/minDetection = UV 220 nmRun Time = 10.7 mink'1 = 3.22α = 1.65reference 46
Methyl Mandelate 2-Methyl-1-Indanone
OH
O
O
CH3
Methyl Mandelate73:27:0.1 H2O/CH3CN/HOAc1 ml/min; 254 nmRun Time = 20 min4.6 mm x 25 cm Whelk-O 1k'1 = 5.27α = 1.15reference 18
O
CH3
2-Methyl-1-Indanone99:1 hexane/IPA1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.00α = 1.12reference 18
95:5:0.5 hexane/IPA/HOAc1 ml/min; 280 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.27α = 1.28reference 26
O
CH3
OEt
O95:5:0.5 hexane/IPA/HOAc1 ml/min; 280 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.75α = 2.53reference 26
O
CH3
OEt
O
95:5:0.5 hexane/IPA/HOAc1 ml/min; 280 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.85α = 1.70reference 26
O
O
O93:7:0.1 hexane/IPA/HOAc1 ml/min; 254 nmrun time = 30 min4.6 mm x 25 cm Whelk-O 1k'1 = 8.10α = 1.21reference 18
20% IPA/hex2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.66α = 1.29reference 7
90:10 hexane/IPA1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.41α = 1.81reference 7
16 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Esters , Lactones, Ketones, Anhydrides
O
CH3
OH
O
H3C
O
H3CO
O
O
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 17
Esters , Lactones, Ketones, Anhydrides REGIS3-Methyl-1-Indanone DPHB
O
CH3
3-Methyl-1-Indanonek'1 = 6.11α = 1.1899:1 hexane/IPA1 ml/min; 254 nmRun Time = 20 min4.6 mm x 25 cm Whelk-O 1reference 18
O
OH
DPHB6% EtOH/hexane1 ml/min; 254 nmRun Time = 41 min4.6 mm x 25 cm Whelk-O 1reference 29
H3C
O
20% IPA/hex2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.17α = 1.66reference 7
Column = L-Leucine25 cm x 4.6 mmMobile Phase = (99.5/0.5)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 11.5 mink'1 = 2.42α = 1.21reference 57
O
S
98:2 hexane/IPA1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 7.82α = 1.12reference 7
OOO
EtOO
H
H
O
OEtO
MeOH/IPA/hexane1 ml/min; 254 nmRun Time = 17 min4.6 mm x 25 cm Whelk-O 1k'1 = 12.73α = 1.16reference 19
10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 2.27α = 1.11reference 26
H3CO
O
OCH3
O
97:3 hexane/IPA1 ml/min; 254 nmRun Time = 27 min4.6 mm x 25 cm Whelk-O 1k'1 = 8.46α = 1.08reference 18 OO
2-Methyl-1-Tetralone Diperodon
1,3,5-Triphenylpent-4-yn-1-one
O
CH3
2-Methyl-1-Tetralone99:1 hexane/IPA1 ml/min; 254 nmRun Time = 12 min4.6 mm x 25 cm Whelk-O 1k'1 = 2.76α = 1.11reference 18
DiperodonColumn = (R)-α-Burke 2 25 cm x 4.6 mmMobile Phase = (48/48/4) CH2Cl2/Hexane/Ethanol
+ 1.5 mM Ammonium AcetateFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 9.0 mink'1 = 1.7α = 1.25reference 46
1,3,5-Triphenylpent-4-yn-1-oneColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase =
Hexane + 0.5% IPA
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 6.5 mink'1 = 1.19α = 1.19reference 46
Column = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase =
(98/2) Hexane/IPA
Flow Rate = 1.0 mL/minDetection =
UV 254 nmRun Time = 20.5 mink'1 = 1.62α = 4.18reference 51
OO
10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 0.67α = 1.16reference 26
Column = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase =
(98/2) Hexane/IPA
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 34.0 mink'1 = 8.00α = 1.44reference 51
Column = D-Phenylglycine25 cm x 4.6 mmMobile Phase = 99/1)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 13.5 mink'1 = 3.10α = 1.18reference 57
Column = (S,S)-β-Gem 125 cm x 4.6 mmMobile Phase = (99.5/0.5)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14.5 mink'1 = 2.67α = 1.43reference 57
18 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Esters , Lactones, Ketones, Anhydrides
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 19
Esters , Lactones, Ketones, Anhydrides REGISBuckminsterfullerene-Enone [2+2] Photoadducts
Semi-prep separation on analytical column
2:1 toluene/hexane1 ml/min; 400 nmRun Time = 22 minSample: 100µ1 of
5 mg/ml solution (0.5 mg)4.6 mm x 25 cm Whelk-O 1reference 8
Tert-butyl-2-(benzamido) cyclopentyl carbamateTert-butyl-2-(benzamido)
cyclopentyl carbamateColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (95/5)Hexane/IPA
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 3.65α = 1.46reference 46
1’-Acetoxychavicol Acetate1’-Acetoxychavicol AcetateColumn = (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (90/10)Hexane/IPA
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 5.94α = 2.05reference 46
Ethyl-2-(p-Hydroxyphenoxy) PropionateEthyl-2-(p-Hydroxyphenoxy)
PropionateColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (98/2)Hexane/Ethanol
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 21.1 mink'1 = 12.72α = 1.15reference 46
20 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Amides, Imides, Carbamates , e tc .
EEDQ
BOC-Ala
CBZ-Val
CBZ-Phe
CBZ nornicotine
N O
O O
EEDQ90:10 hexane/IPA1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.53α = 2.13reference 18
k'1 = 1.75
NO
N
O
Omethanol2 ml/min; 254 nmRun Time = 6 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.75α = 1.20reference 7
CBZ nornicotine
N
N
O O
CBZ nornicotine1:3 MeOH/dichloromethane1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm
Whelk-O 1k'1 = 0.37α = 1.38reference 7
O N
O
H
OH
O
CBZ-Phe95:5:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 40 min4.6 mm x 25 cm Whelk-O 1k'1 = 10.2α = 1.20reference 18
O N
O
H
OH
O
CBZ-Val95:5:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 19 min4.6 mm x 25 cm
Whelk-O 1k'1 = 5.49α = 1.13reference 18
O N
O
H
CH3
OH
O
BOC-Ala98:2:0.2 hexane/IPA/HOAc1 ml/min; 220 nmRun Time = 17 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.43α = 1.09reference 18
15% EtOH/hexane1 ml/min; 254 nmRun Time = 16 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.79α = 1.66reference 18
ON
O
O
H
80:20:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm
Whelk-O 1k'1 = 5.97α = 1.36reference 18 N
O
OH
Ph
Ph
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 21
Amides, Imides, Carbamates , e tc . REGIS
CH3
NH
O
H
ethyl acetate1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.50α = 1.56reference 7
CH3
NH
O
CH3
ethyl acetate1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.64α = 2.06reference 26
CH3
NH
O
ethyl acetate1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.16α = 5.56reference 7
CH3
N
O
2%EtOH/hex1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.13α = 1.03reference 26
ethyl acetate1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 0.14α = 3.21reference 26
N OH
Me Et
95:5:0.5 hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 14.97α = 1.12reference 7
20% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.45α = 1.34reference 26
Np-Ts
10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.64α = 1.11reference 26
Np-Ts
k'1 = 0.14
α = 3.21
CH3
NH
O
N
CH3
H
CH3
O20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 3.72α = 3.17reference 38
N
CH3
H
O
Cl
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.48α = 11.6reference 38
N
CH3
H
CH3
O
I
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 4.10α = 5.12reference 38
N
CH3
H
O
Br
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.75α = 13.7reference 38
N
CH3
H
O
Br
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.61α = 12.8reference 38
N
CH3
H
O20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.39α = 6.74reference 38
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 10.87α = 1.29reference 38
N
CH3
H
O
F
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.17α = 7.29reference 38
P
NH
O
OEt
OEtH3C
CH3
22 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Amides, Imides, Carbamates , e tc .
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 23
Amides, Imides, Carbamates , e tc . REGIS
P
NH
O
OEt
OEtH3C
CH3
F
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 0.83α = 1.39reference 38
P
NH
O
OEt
OEtH3C
CH3
Cl
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 0.84α = 1.55reference 38
P
NH
O
OEt
OEtH3C
CH3
Br
20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 0.86α = 1.66reference 38
N
H
O
Br
Br
D
H
H
H
H
D
D D
10% acetonitrile in CO2
(S,S) Whelk-O 1k'1 = 19.7α = 1.025reference 39
N
H
O
H
D
D
H
H
H
H
D
D D
10% acetonitrile in CO2
(S,S) Whelk-O 1k'1 = 8.5α = 1.025reference 39
N
H
O
D
H
H
H
H
D
D D
TMS
TMS
10% acetonitrile in CO2
(S,S) Whelk-O 1k'1 = 25α = 1.025reference 39
Column = (R,R)-Whelk-O 125 cm x 4.6 mm
Mobile Phase = (80/20)Hexane/IPA Flow Rate = 2.0mL/minDetection = UV 254nmRun Time = 19.0 mink'1 = 7.53α = 1.77reference 52
Column = (S,S)-Whelk-O 125 cm x 4.6 mm
Mobile Phase = (90/10)Hexane/IPA
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 46.0 mink'1 = 2.70α = 6.02reference 51
24 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Amides, Imides, Carbamates , e tc .
REGIS Epoxides
Styrene Oxide Stilbene Oxide
m-Cl Styrene Oxide
OStyrene Oxide1% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.37α = 1.37reference 18
O
Stilbene Oxide10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.45α = 2.00reference 18
O
0.1% HOAc in hexane1 ml/min; 254 nmRun Time = 20 min4.6 mm x 25 cm Whelk-O 1k'1 = 5.92α = 1.12reference 18
OCl
m-Cl Styrene Oxidehexane1 ml/min; 220 nm4.6 mm x 25 cm
Whelk-O 1reference 30
β-Lactam Cyclopentyl Benzoyl-Diamideβ-LactamColumn: (S,S)-
DACH-DNB25 cm x 4.6 mmMobile Phase: (48/48/2)
Hex/CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.0 mink’1: 3.40α: 1.33reference 59
Cyclopentyl Benzoyl-DiamideColumn: (S,S)-ULMO
25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/IPAFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 8.7 mink’1: 2.62α: 1.47reference 46
Alcohols REGIS
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 25
Ibuprofenol 1,2,3,4-Tetrahydro-1-Naphtol
9-Anthryl Trifluoromethyl Carbinol
α-Naphthyl Methyl Carbinol
Acenaphthenol
Tert Butyl Phenyl Carbinol
CH3
OH
Ibuprofenol99:1 hexane/IPA1 ml/min; 254 nmRun Time = 14 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.38α = 1.05reference 26
OH
1,2,3,4-Tetrahydro-1-NaphtolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 2.17α = 1.30reference 46
Tert Butyl Phenyl CarbinolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPA Flow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 6.0 mink'1 = 4.60α = 1.46reference 46
CH3
OH
α-Naphthyl Methyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14.5 mink'1 = 3.49α = 1.25reference 46
9-Anthryl TrifluoromethylCarbinol
Column = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10 mink'1 = 1.36α = 2.02reference 46
HO CF3
AcenaphthenolColumn: (R,R)-ULMO25 cm x 4.6 mmMobile Phase: (95/5)
Hexane/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 10 mink’1: 1.68α: 1.46reference 46
OH
2% IPA/hexane1 ml/min; 220 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.76α = 1.13reference 18
H3COH
80:20 hexane/IPA1 ml/min; 254 nmrun time = 10 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.22α = 2.08reference 26
OH
Beta Naphthyl Methyl Carbinol 1,1’-Bi-2-Naphthol
1-Naphthyl-2-butanol
9-Anthrylethanol
2-Naphthyl-2-butanol
Tetrahydrobenzopyrene-7-ol
1,1’-Bi-2-NaphtholColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98/2)
Hexane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 18.0 mink'1 = 4.84α = 1.24reference 48
9-AnthrylethanolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (95/5) Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 12 mink'1 = 1.82α = 1.74reference 48
2-Naphthyl-2-butanolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)
Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 8 mink'1 = 1.00α = 1.93reference 48
Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (99/1)
Hexane/IPA Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 18.5 mink'1 = 5.59α = 1.09reference 55
CH3
OH
Beta Naphthyl Methyl CarbinolColumn: (R,R)-ULMO25 cm x 4.6 mmMobile Phase: (97/3) Hexane/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 9 mink’1: 1.64α: 1.34reference 46
OH
Tetrahydrobenzopyrene-7-ol80:20 hexane/IPA1 ml/min; 254 nmrun time = 22 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.10α = 1.18reference 18
1-Naphthyl-2-butanolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)
Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 6 mink'1 = 0.80α = 1.35reference 48
CH3
OH
1% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.38α = 1.05reference 7
26 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Alcohols
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 27
Alcohols REGIS 1-Phenylpentanol Phenyl Tribromomethyl Carbinol
Phenyl Propyl Carbinol
Phenyl Ethyl Carbinol
1,1,2,-Triphenyl-1,2-Ethanediol
Phenyl Methyl Carbinol
1-PhenylpentanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (99/1)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 7.0 mink'1 = 1.65α = 1.45reference 60
CBr3
OHPhenyl Tribromomethyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 9 mink'1 = 1.87α = 1.25reference 46
CH3
OH
Phenyl Methyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = 100%
HexaneFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14 mink'1 = 3.11α = 1.30reference 46
OH
Phenyl Ethyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 6.5 mink'1 = 1.06α = 1.30reference 46
Phenyl Propyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = 100% HexaneFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 12 mink'1 = 2.25α = 1.56reference 46
OH
1,1,2,-Triphenyl-1,2-EthanediolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 13 mink'1 = 2.59α = 1.14reference 48
OHColumn = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (80/20)
Hexane/IPA Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 24.0 mink'1 = 13.30α = 1.11reference 55
Column = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10 mink'1 = 1.97α = 1.37reference 48
28 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Alcohols
1,1’-Binaphthol Monomethylether Terfenadine
2-Methoxyphenyl Phenyl Carbinol
Trans Phenyl Cyclohexanol Analytical vs. Preparative Run
Phenyl cyclohexyl carbinol
Propafenone
Phenyl phenylethyl carbinolPhenyl isopropyl carbinol
1,1'-BinaphtholMonomethyletherColumn: (S,S)-ULMO 25 cm
x 4.6 mmMobile Phase: (98/2)
Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 11.0 mink'1 = 2.23α = 1.28reference 48
TerfenadineColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (97/3)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 15.0 mink'1 = 5.91α = 1.20reference 46
PropafenoneColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (47/47/6)
CH2Cl2/Hexane/Ethanol + 0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.99α = 1.25reference 46
Trans Phenyl CyclohexanolAnalytical vs. Preparative Run
Column = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPA Flow Rate = 1.0 mL/minDetection = UV 270 nmRun Time = 7.0 minreference 48
2-Methoxyphenyl Phenyl CarbinolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPA Flow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 12.0 mink'1 = 2.92α = 1.13reference 48
Phenyl cyclohexyl carbinolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (99/1)
Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 6.5 mink'1 = 0.97α = 1.39reference 48
Phenyl isopropyl carbinolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time: 6 mink'1 = 0.86α = 1.38reference 48
Phenyl phenylethyl carbinolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)
Heptane/IPAFlow Rate = 1.0 mL/min Detection = UV 215 nmRun Time = 9.5 mink'1 = 1.81α = 1.30reference 48
2.8 MG
1.4 MG
0.14 MG
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 29
Alcohols REGIS Methyl 3-phenyl-3azido-2hydroxypropanoate
(Erythro-diastereomer)1-(4-Methoxyphenyl)-2-butanol
2-Thiopheneethanol
1-Phenyl-2-propanol
3-Thiopheneethanol
1-(4-Methoxyphenyl)-2-propanol
1-(o-Methoxyphenyl) Ethanol1-(4-Hydroxyphenyl) Ethanol
1-(4-Methoxyphenyl)-2-butanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 12.0 mink'1 = 2.04α = 1.49reference 60
1-Phenyl-2-propanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 6.5 mink'1 = 1.72α = 1.19reference 60
3-Thiopheneethanol Column = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 11.5 mink'1 = 2.42α = 1.13reference 60
1-(o-Methoxyphenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.27α = 1.29reference 60
Methyl 3-phenyl-3azido-2hydroxypropanoate(Erythro-diastereomer)
Column = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (97/3)
Heptane/GlymeFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Tim = 10.5 mink'1 = 2.34α = 1.16reference 48
1-(4-Methoxyphenyl)-2-propanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 17.5 mink'1 = 5.33α = 1.28reference 60
2-Thiopheneethanol Column = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 2.21α = 1.12reference 60
1-(4-Hydroxyphenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (95/5)
n-Heptane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 1.491α = 1.16reference 60
30 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Alcohols
1-[(4-Phenyl) phenyl] Ethanol 1-(4-Benzyloxy) phenyl Ethanol
1-(m-Trifluoromethylphenyl) Ethanol
1-(p-Flurorophenyl) Ethanol
1-(p-Methylphenyl) Ethanol
1-(p-Bromophenyl) Ethanol
1-(o-Methylphenyl) Ethanol1-(m-Methylphenyl) Ethanol
1-(4-Benzyloxy) phenyl EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 5.21α = 1.21reference 60
1-(p-Flurorophenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 2.13α = 1.16reference 60
1-(p-Methylphenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 2.06α = 1.21reference 60
1-(o-Methylphenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 1.88α = 1.29reference 60
1-[(4-Phenyl) phenyl] EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 3.76α = 1.21reference 60
1-(p-Bromophenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 11.5 mink'1 = 2.39α = 1.17reference 60
1-(m-Trifluoromethylphenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 9.0 mink'1 = 1.66α = 1.14reference 60
1-(m-Methylphenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 1.94α = 1.26reference 60
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Alcohols REGIS 1-(o-Chlorophenyl) Ethanol 1-(p-Chlorophenyl) Ethanol
1-(m-Chlorophenyl) Ethanol
1-(p-Chlorophenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 2.18α = 1.15reference 60
1-(o-Chlorophenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 1.58α = 1.12reference 60
RanolazineRanolazineColumn = (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (65/35)
Hexane/IPA + 35 mMAmmonium Acetate
Flow Rate = 2.0 mL/minDetection = UV 220 nmk'1 = 11.51α = 1.23reference 46
1-(m-Chlorophenyl) EthanolColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (98.5/1.5)
n-Heptane/1,2-Dimethoxyethane
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10.5 mink'1 = 2.13α = 1.17reference 60
Phenylethylene GlycolPhenylethylene GlycolColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (99/1)
Hexane/EthanolFlow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 18.7 mink'1 = 11.62α = 1.11reference 46
Benzoin
32 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Hydrobenzoin
Ipsdienol
Anisoin
O
OH
Benzoin80:20:0.5 hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.86α = 1.97reference 7
O
OHH3CO
OCH3Anisoin80:20:0.5hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 3.07α = 2.34reference 26
60:40 hexane/EtOH1 ml/min; 240 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.03α = 1.32reference 26
OH
OH
Hydrobenzoin95:5 hexane/IPA1 ml/min; 254 nmRun Time = 18 min4.6 mm x 25 cm Whelk-O 1k'1 = 1.14α = 1.40reference 18
OH
OH
98:2:0.5 hexane/EtOH/HOAc1 ml/min; 240 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.20α = 1.28reference 26
Ipsdienol2% IPA/hexane1 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm
Whelk-O 1k'1 = 0.95α = 1.21reference 18
HO
OH
OH
98:2:0.5 hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 7.54α = 1.08reference 7
REGIS Diols , Hydroxyketones, e tc .
OH
OHH3CO
OCH3
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Sulfoxides REGIS
SCH3
OOH3C
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 9 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.10α = 1.13reference 18
SCH3
O7:2:1 hexane/IPA/CH2C121 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 3.83α = 1.24reference 7
SCH3
O
Br
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.75α = 1.13reference 18
H3C
S
O
CH3
80:20 hexane/IPA1.5 ml/min; 254 nmRun Time = 14 min4.6 mm x 25 cm Whelk-O 1k'1 = 2.11α = 1.70reference 31
SCH3
O
Br
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.75α = 1.13reference 18
S
O
CH3
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 6 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.90α = 1.46reference 18
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 11 min4.6 mm x 25 cm
Whelk-O 1k'1 = 5.04α = 1.12reference 18
S S O
7:2:1 hexane/IPA/CH2C121 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.29α = 2.14reference 7
SCH3
O
34 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Sulfoxides
k'1 = 10.72
S
O
O
SCH3
O
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmrun time = 11 min4.6 mm x 25 cm
Whelk-O 1k'1 = 5.02α = 1.21reference 18
7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmrun time = 6 min4.6 mm x 25 cm
Whelk-O 1k'1 = 10.72α = 1.19reference 18
Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (27.5/27.5/45)
CH2Cl2/Dioxane/HexFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 35.0 mink’1: 10.30α: 1.15reference 59
Column: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase:
(98/2) CH2Cl2/IPA
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 16.0 mink’1: 2.34α: 2.07reference 59
Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (98/2)
CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 13.0 mink’1: 3.08α: 1.26reference 59
Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase:
(98/2) CH2Cl2/IPA
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 17.0 mink’1: 3.33α: 1.63reference 59
OmeprazoleSulfinpyrazoneOmeprazoleColumn = (S)-α-Burke 2 25 cm x 4.6 mmMobile Phase = (95/5) CH2Cl2/CH3OHFlow Rate = 1.0 mL/minDetection = UV 302 nmRun Time = 8.0 mink'1 = 0.64α = 3.04reference 46
SulfinpyrazoneColumn = (R,R)-Whelk-O 1 25 cm x 4.6 mmMobile Phase = (75/25) Hexane/Ethanol
+ 15 mM Ammonium AcetateFlow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.74α = 1.35reference 46
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Sulfoxides REGIS
Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (40/40/20)
CH2Cl2/Dioxane/HexFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 27.0 mink’1: 7.51α: 1.21reference 59
Column: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase: (27.5/27.5/45)
CH2Cl2/Dioxane/HexFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 18.0 mink’1: 4.77α: 1.18reference 59
Column: (R,R)-DACH-DNB
25 cm x 4.6 mmMobile Phase:
(27.5/27.5/45) CH2Cl2/Dioxane/Hex
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 20.0 mink’1: 5.16α: 1.26reference 59
Column: (R,R)-DACH-DNB
25 cm x 4.6 mmMobile Phase: (95/5)
CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 15.0 mink’1: 2.15α: 2.05reference 59
PantoprazolePantoprazoleColumn = (R)-α-Burke 2
25 cm x 4.6 mmMobile Phase = (48/48/4)
CH2Cl2/Hexane/Ethanol + 4 mM Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 280 nmRun Time = 12.0 mink'1 = 4.07α = 1.38reference 46
36 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Phosphorous Compounds
P
N
O
OEt
OEt
H
H3CO
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.26α = 1.50reference 40
P
N
O
OEt
OEt
H
F3CO5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.72α = 1.26reference 40
P
N
O
OEt
OEt
H
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.26α = 1.26reference 40
P
N
O
OEt
OEt
H
OCF35% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.05α = 1.63reference 40
P
N
O
OEt
OEt
H
OCF35% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.10α = 2.08reference 40
P
N
O
OEt
OEt
H
F
F
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.09α = 1.31reference 40
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.58α = 1.23reference 40
P
N
O
OEt
OEt
H
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 9.61α = 1.75reference 40
P
N
O
OEt
OEt
H
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 37
Phosphorous Compounds REGIS
Cyclophosphamide Tertiary Phosphine Oxide
Secondary Phosphine OxidePhosphine Selenium Oxide
P
N
O
OEt
OEt
H
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.87α = 5.12reference 40
5:4:1 hexane/CH2C12/CH3CN1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.11α = 1.15reference 7
Tertiary Phosphine OxideColumn: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase:
(37.5/37.5/25) Hex/Dioxane/IPA
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.0 mink'1: 2.19α: 1.48reference 59
Secondary Phosphine OxideColumn: (S,S)-DACH-DNB 25 cm x 4.6 mmMobile Phase: (75/25) CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 19.0 mink'1: 1.49α: 4.11reference 59
P
N
O
OEt
OEt
H
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 7.35α = 2.54reference 40
P
N
O
OEt
OEt
H
N
5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 12.30α = 2.00reference 40
CyclophosphamideColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (95/5)
Hexane/EthanolFlow Rate = 1.5 mL/minDetection = UV 195 nmRun Time = 16.0 mink'1 = 6.31α = 1.27reference 46
Phosphine Selenium OxideColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (70/30)
Hex/CH2Cl2Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 13.0 mink'1: 2.49α: 1.48reference 59
38 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Secondary Phosphine Oxide Tertiary Phosphine Oxide
Tertiary Phosphine OxideSecondary Phosphine Oxide
Tertiary Phosphine OxideColumn: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase:
(42.5/42.5/15) Hex/Dioxane/IPA
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 28.0 mink'1: 8.11α: 1.17reference 59
Tertiary Phosphine OxideColumn:
(R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase: (40/40/20)
Hex/Dioxane/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.0 mink’1: 4.19α: 1.25reference 59
10% EtOH/hexane1 ml/min; 254 nmrun time = 13 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.07α = 1.17reference 18
P
OH
O
OCH3
OCH3
Secondary Phosphine OxideColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (90/10)
CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 8.0 mink'1: 1.23α: 1.81reference 59
Secondary Phosphine OxideColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase:
(90/10) CH2Cl2/IPA
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.5 mink'1: 2.20α: 1.97reference 59
10% IPA/hex2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.35α = 3.53reference 7
N
N
PO
H
EtOEtO
P
OH
O
OCH3
OCH3
10% EtOH/hexane1 ml/min; 254 nmrun time = 18 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.75α = 1.38reference 18
REGIS Phosphorous Compounds
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 39
Atropisomers REGIS
CH3
O NEt
EtEtOAc1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 0.46α = 2.17reference 7
O
O
10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 2.26α = 1.11reference 7
CH3
CH3
N
SO
CH3
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.73α = 1.64reference 7
CH3
O N
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O-1k'1 = 3.23α = 2.66reference 10
N
SS
CH3
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.91α = 2.13reference 7
CH3
O N
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.29α = 2.46reference 10
CH3
O N
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O-1k'1 = 6.24α = 2.63reference 10 CH3
O N
80:20:0.1%hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O-1k'1 = 4.46α = 2.08reference 10
40 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Atropisomers
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 10.06α = 2.37reference 41
NO
O
NO
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 13.00α = 2.57reference 41
NO
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 14.18α = 2.78reference 41
NO
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 15.59α = 3.74reference 41
NO
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 12.41α = 2.74reference 41
NO
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 16.29α = 3.15reference 41
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.29α = 2.25reference 41
NO
O
Cl
Cl
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.06α = 2.22reference 41
NO
O
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Atropisomers REGIS
sulfoxide atropisomer
sulfone atropisomersulfone atropisomer
CH3
O N
CH3
mixture of stereoisomers80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 10
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1(S)(-) retained on (S,S) CSPk'1 = 1.71α = 3.09reference 10
CH3
O N
sulfoxide atropisomerZ diastereomer2% MeOH in CH2Cl22 ml/min; 300 nm, -40o C4.6 mm x 25 cm Whelk-O 1k'1 = 1.32α = 4.06reference 21
CH3
SO
sulfone atropisomer-80°Creference 22
CH3
SO
H3C
SO
CH3
O N
O
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 7.95α = 2.43reference 10
CH3
O N
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.05α = 3.00reference 10
80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.11α = 2.04reference 10 CH3
O N
CH3
S OO
sulfone atropisomer2% MeOH in CH2Cl22 ml/min; 300 nm, -80°C4.6 mm x 25 cm Whelk-O 1k'1 = 0.54α = 5.79reference 21
42 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Atropisomers
NS
O
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.06α = 2.48reference 41 N
S
O
HO
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.00α = 3.43reference 41
NS
O
Br
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.25α = 3.20reference 41
NS
O
MeO
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.65α = 3.63reference 41
NS
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.06α = 4.34reference 41
NS
OCl
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.94α = 1.12reference 41
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.78α = 1.90reference 41N
S
O
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.41α = 1.80reference 41
NS
O
NO
O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 7.12α = 2.40reference 41
NO
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O CSPk'1 = 6.94α = 1.36reference 41
NO
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.65α = 1.35reference 41
NO
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.65α = 1.50reference 41
NO
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 7.41α = 1.48reference 41
NO
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 7.12α = 1.36reference 41
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.06α = 2.21reference 41
NO
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.65α = 1.64reference 41 N
S
O
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 43
Atropisomers REGIS
44 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Atropisomers
NS
S
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.94α = 1.85reference 41 N
S
O
Cl
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.24α = 1.45reference 41
NS
S
HO
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.59α = 1.70reference 41
NS
S
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.82α = 1.62reference 41
NS
S
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.12α = 2.39reference 41
NS
S
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.12α = 1.62reference 41
15% IPA/hexane1 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.86α = 1.86reference 42
N
N
O
S
15% IPA/hexane1 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.14α = 5.56reference 42
N
N
O
S
O2N
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 45
Atropisomers REGIS
NS
OCl
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.12α = 2.21reference 41 N
S
S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.41α = 1.66reference 41
NS
S
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.82α = 1.75reference 41
NS
S
HO
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.53α = 1.84reference 41
NS
S
HO
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.41α = 2.61reference 41
NS
S
Br
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.24α = 2.02reference 41
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.29α = 1.80reference 41N
S
S
Cl
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.18α = 1.46reference 41 N
S
S
46 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Atropisomers
Amlodipine Vapol
Adam’s Acid DiethylamideNimodipine
AmlodipineColumn = (R,R)-
Whelk-O 125 cm x 4.6 mm
Mobile Phase = (46/46/8)CH2Cl2/Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 13.0 mink'1 = 5.13α = 1.22reference 46
OH
OH
Ph
Ph
VapolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase =
100% MethanolFlow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 13 mink'1 = 1.74α = 3.37reference 48
NimodipineColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase =
(65/35)Methanol/H2O
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 31.0 mink'1 = 9.25α = 1.13reference 46
Adam’s Acid DiethylamideColumn = (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase = (70/30)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 17.0 mink'1 = 4.11α = 1.27reference 46
15% IPA/hexane1 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 11.8α = 1.58reference 42
N
N
O
N
F
N
NH2
O
O
20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.00α = 2.25reference 41
NS
S
Phototrigger 1 Phototrigger 2
Phototrigger 3
MesogensPhototrigger 4
O
H H
Phototrigger 18% IPA in hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 24
O
H3C CH3
Phototrigger 28% IPA in hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 24
O
H3C CH3
O
N
H
H3C
H3C
Phototrigger 440% IPA in hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 24
O
O
CN
O
O
O
CN
MesogensSchuster's candidate photoresolvable mesogensepoxide derivatives reference 13
Phototrigger 340% IPA in hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 24
Optical Switches, Liquid Crystal Components , e tc . REGIS
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 47
48 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Allenes
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.74α = 2.38reference 42
H
•
CH3
O
O
Cl
H
•
CH3
O
O
F95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.72α = 2.33reference 42
H
•
CH3
O
O
O2N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.20α = 1.59reference 42
H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.43α = 3.23reference 42
H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.87α = 2.90reference 42
H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.69α = 3.70reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.95α = 4.19reference 42
H
•
CH3
O
OH
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.99α = 7.49reference 42
H
•
CH3
O
OH
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H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.84α = 3.46reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.79α = 3.23reference 42
H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.64α = 3.29reference 42
H
•
CH3
O
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.79α = 2.41reference 42
H
•
CH3
O
O
Br
H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.84α = 5.68reference 42
H CH3
H
•
CH3
O
O
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.33α = 3.13reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.93α = 3.85reference 42
H
•
CH3
O
O
H
•
CH3
O
O
I
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.85α = 2.48reference 42
Allenes REGIS
REGIS Allenes
50 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
H
•
CH3
O
OH
O2N95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.94α = 1.74reference 42
H
•
CH3
O
N
CH3
CH3
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 7.96α = 1.03reference 42
H
•
CH3
O
N
H
CH3
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 10.07α = 1.45reference 42
H
•
CH3
O
N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.47α = 0.09reference 42
H
•
CH3
O
N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.00α = 1.14reference 42
H
•
CH3
O
N
H
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 7.10α = 1.44reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.14α = 1.08reference 42
H
•
CH3
O
N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.76α = 1.13reference 42
H
•
CH3
O
N
H
•
CH3
O
OH
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.90α = 3.92reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.88α = 3.62reference 42
H
•
CH3
O
OH
H3CO
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.01α = 2.67reference 42
H
•
CH3
O
OH
Br
k'1 = 0.90α = 2.5795:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1reference 42
H
•
CH3
O
OH
F
H
•
CH3
O
OH
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.53α = 3.56reference 42
H
•
CH3
O
OH
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.04α = 4.28reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 1.07α = 2.84reference 42
H
•
CH3
O
OH
I
H
•
CH3
O
OH
Cl
k'1 = 0.92α = 2.6795:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1reference 42
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 51
Allenes REGIS
REGIS Allenes
52 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
H
•
CH3
O
N
H
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.46α = 1.34reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.47α = 1.14reference 42
H
•
CH3
O
N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 10.30α = 1.11reference 42
H
•
CH3
O
N
H
•
CH3
O
N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.10α = 1.18reference 42
H
•
CH3
O
N
H
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.21α = 1.33reference 42
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.30α = 1.06reference 42
H
•
CH3
O
N
CH3
H
•
CH3
O
N
95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.07α = 1.12reference 42
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 53
Organometal l ic Compounds REGIS
(OC)3Cr O
H3CO
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.82α = 1.07reference 20
(OC)3Cr O
H3CO
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.93α = 1.18reference 20
(OC)3Cr O
CH3
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.25α = 1.19reference 20
k'1 = 1.71
(OC)3Cr
NH
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.71α = 1.75reference 20
k'1 = 6.79
(OC)3Cr
N
OCH3
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 6.79α = 1.04reference 20
(OC)3Cr O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.48α = 1.23reference 20
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.44α = 1.75reference 20
(OC)3CrCH3
NH
O CH3
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.93α = 1.62reference 20
k'1 = 2.44
(OC)3CrCH3
NH
O
REGIS Organometal l ic Compounds
54 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
k'1 = 1.79
α 1 99
(OC)3CrCH3
NH
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.79α = 1.99reference 20
(OC)3CrCH3
NH
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.14α = 1.86reference 20
k'1 = 1.14
(OC)3Cr
NH
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.14α = 1.75reference 20
k'1 = 11.86
(OC)3Cr
N
O CH3
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 11.86α = 2.08reference 20
k'1 = 1.86
(OC)3CrOEt
NH
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.86α = 1.69reference 20
k'1 = 3.71
(OC)3Cr
N
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.71α = 2.50reference 20
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.29α = 2.46reference 20
(OC)3Cr
N
O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.71α = 2.50reference 20
k'1 = 2.29
(OC)3Cr
N
O
H
O
CH3
(OC)3Cr
30% CH2Cl2 in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.28α = 1.07reference 20
H
O
OCH3
(OC)3Cr
30% CH2Cl2 in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 7.57α = 1.09reference 20
CH3
O
CH3
(OC)3Cr
30% CH2Cl2 in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.57α = 1.06reference 20
(OC)3Cr O
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.48α = 1.08reference 20
OH
CH3
(OC)3Cr
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.77α = 1.11reference 20
OH
OCH3
(OC)3Cr
20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.22α = 1.15reference 20
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 55
Organometal l ic Compounds REGIS
REGIS Agricul tural Compounds
56 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
PPO Inhibitor PPO Inhibitor
Tetramethrin
PPO Inhibitor
Bromacil
PPO Inhibitor
Mecoprop MethylPermethrin
O2N
O
O
N N
Et
O NH
CH3
Cl
CF3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 5.2α = 1.32reference 23
O2N
O
O
N N
CH3
O NH
CH3
Cl
CF3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 7.5α = 1.29reference 23
O2N
O
O
N N
CH3
O NH
H
Cl
CF3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 8.0α = 1.22reference 23
O2N
N
O
N N
CH3
O NH
CH3
Cl
CF3
H
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 15.1α = 1.04reference 23
Tetramethrin (insecticide)2% IPA/hexane1 ml/min; 254 nmRun Time = 22 min4.6 mm x 25 cm
Whelk-O 1k'1 = 11.77α = 1.12reference 43
O
O
N
O
O
Bromacil (insecticide)2% IPA/hexane1 ml/min; 254 nmRun Time = 38 min4.6 mm x 25 cm
Whelk-O 1k'1 = 21.43α = 1.07reference 43
N
NH3C
Br
O
H
O
Cl
Cl
O
O
O
Permethrin (insecticide)0.2% IPA/hexane1 ml/min; 254 nmRun Time = 16 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.83 cis; 7.46 transα = 1.11 cis; 1.24 transreference 43
O
CH3
O
OCH3
Cl
CH3
Mecoprop Methyl (insecticide)hexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.92α = 1.15reference 43
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 57
Agricul tural Compounds REGISResmethrin Metalaxyl
Sethoxydim
Metolachlor
Chrysanthemic Acid-Ethyl Ester
Leptophos, Phosvel
MecopropOmite
ResmethrinColumn: (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase: 100% HexaneFlow Rate:1.0 mL/minDection: UV 254 nmRun Time: 15.0 mink'1 = 6.30α = 1.19reference 46
N
CH3
CH3
CH3
O
OCH3
O
OCH3
Metalaxyl (herbicide)70:30 hexane/IPA1 ml/min; 254 nmRun Time = 13 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.54α = 1.13reference 43
PO
S
OCH3
Cl
Cl
Br
Leptophos, Phosvel (insecticide)
hexane1 ml/min; 254 nmRun Time = 10 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.11α = 1.18reference 43
N
CH3
CH3
CH3
OCH3
O
Cl
Metolachlor (herbicide)2% IPA/hexane1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm
Whelk-O 1reference 43
Sethoxydim (herbicide)2% IPA/hexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.77α = 1.26reference 43
NO
OH
O
S
Chrysanthemic acid ethyl ester(mixture of isomers)hexane1 ml/min; 254 nmRun Time = 10 min4.6 mm x 24 cm
Whelk-O 1reference 43
O
O
Et
Omite (acaricide)(mixture of isomers)hexane1 ml/min; 254 nmRun Time = 25 min4.6 mm x 24 cm
Whelk-O 1reference 43
O
CH3
OH
OCH3
Cl
Mecoprop (herbicide)99:1:0.1 HEX/IPA/HOAc1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.54α = 1.13reference 43
O
OS
O
OOmite
REGIS Agricul tural Compounds
58 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Propiconazole, Tilt Devrinol, Napropamide
Diclofop Methyl
Crotoxyphos
Diclofop Methyl
Chlorflurecol Methlyl
PPO InhibitorPPO Inhibitor
Cl
OOCl
N
NN
Propiconazole, Tilt (fungicide)
99:1:0.1 IPA/hexa-ne/HOAc1 ml/min; 254 nmRun Time = 70 min4.6 mm x 25 cm
Whelk-O 1reference 43
O
CH3
N
O
Devrinol, Napropamide (herbicide)1:1 IPA/hexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.17α = 3.00reference 43
HO
Cl
O
OCH3
Chlorflurecol Methyl(herbicide)2% IPA/hexane1ml/min; 254 nmRun Time 16 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.96α = 1.28reference 43
Crotoxyphos70:30 hexane/IPA1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.37α = 1.93reference 43
Diclofop Methyl (herbicide)1% IPA/hexane1 ml/min; 254 nmRun Time = 30 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.29α = 1.21reference 43 O
Cl
Cl
CH3
O
O
CH3O
Diclofop Methyl (herbicide)hexane1 ml/min; 254 nmRun Time = 30 min4.6 mm x 25 cm
Whelk-O 1k'1 = 14.19α = 1.30reference 43 O
Cl
Cl
CH3
O
O
CH3O
O2N
O
O
N N
CH3
O OCH3
Cl
CF3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 3.9α = 1.11reference 23
O2N
O
O
N N
Et
O OEt
Cl
CF3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 2.4α = 1.12reference 23
cis:trans Cypermethrin PPO Inhibitor
Tetramisole
PPO Inhibitor
Silvex Methyl
PPO Inhibitor
cis:trans CypermethrinColumn = (3R,4S)-Pirkle 1-J
25 cm x 4.6 mmMobile Phase = (98/2)
Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 22.0 mink'1 (trans) = 4.59α (trans) = 1.19k'1 (cis) = 6.19α (cis) = 1.18reference 46
O2N
O
O
N N
CH3
O OEt
Cl
CF3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.2α = 1.08reference 23
O2N
O
O
N N
CH3
O O
Cl
CF3
OCH3
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 6.1α = 1.08reference 23 O2N
O
O
N N
CH3
O O
Cl
CF3
OEt
PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.2α = 1.10reference 23
TtetramisoleColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (40/40/20)
CH2Cl2/Hexane/Ethanol + 0.01 M Ammonium Acetate
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 7.0 mink'1 = 0.52α = 2.84reference 46
Silvex Methyl (herbicide)
hexane1 ml/min; 254 nmrun time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.47α = 1.05reference 43
O
CH3
O
OCl
Cl
CH3
Cl
Column = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = Hexane Flow Rate = 0.5 mL/minDetection = UV 254 nmRun Time = 15.5 minreference 54
Column = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = Hexane Flow Rate = 0.5 mL/minDetection = UV 254 nmRun Time = 18.5 minreference 54
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Agricul tural Compounds REGIS
REGIS Agricul tural Compounds
60 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Fluazifop-butyl Haloxyfop-ethoxyethyl
Dinocap
Quizalofop-ethylFenoxaprop-ethyl
Fluazifop-butylColumn: (S,S)-DACH-DNB
25 cm x 4.6 mmMobile Phase: (95/5)
Hexane/IPATemperature: 20º CFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 11.5 mink'1 = 2.65α = 1.22reference: 59
Haloxyfop-ethoxyethylColumn: (S,S)-DACH-DNB
25 cm x 4.6 mmMobile Phase: (95/5)
Hexane/IPATemperature: 20º CFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 13.0 mink'1 = 3.13α = 1.25reference: 59
Fenoxaprop-ethylColumn: (R,R)-DACH-DNB
25 cm x 4.6 mmMobile Phase: (95/5)
Hexane/IPATemperature: 20º CFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 18.0 mink'1 = 4.70α = 1.15reference: 59
FenvalerateFenvalerateColumn: (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase: (99/1)
Hexane/IPAFlow Rate: 3.0 mL/minDetection: UV 254 nmk'A1= 9.36α(A1,A2)= 2.54k'B1= 16.79α(B1,B2)= 1.14reference 46
Quizalofop-ethylColumn: (R,R)-DACH-DNB
25 cm x 4.6 mmMobile Phase: (95/5)
Hexane/IPATemperature: 20º CFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 20.0 mink'1 = 5.22α = 1.21reference: 59
Dinocap (fungicide) - mixture of isomershexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm Whelk-O 1reference 43
O2N
NO2
O
O2N NO2
O
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 61
Miscel laneous Pharmaceut icals REGISNirvanol Mephenytoin
Cyclothiazide
Oxazepam
Bendroflumethiazide
Thalidomide
N
N O
H
HO
CH3
Nirvanol20% IPA/hexane1 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.50α = 2.57reference 31
N
N O
H
CH3O
CH3
Mephenytoin20% IPA/hexane1 ml/min; 254 nmRun Time = 14 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.57α = 2.46reference 31
N
N
O
H
OO
O
Thalidomide63:37:0.1 H2O/MeOH/HOAc1 ml/min; 254 nmRun Time = 33 min4.6 mm x 25 cm
Whelk-O 1k'1 = 10.19α = 1.10reference 18
OxazepamColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (75/25)
Hexane/IPA + 0.01 MAmmonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 9.5 mink'1 = 2.73α = 1.56reference 46
CyclothiazideColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (75/25)
Hexane/IPA + 0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 12.0 mink'1 = 3.71α = 1.47reference 46
bendroflumethiazidek'1 = 7.89α = 1.161:1 hexane/IPA1 ml/min; 220 nmrun time = 30 min4.6 mm x 25 cm
Whelk-O 1reference 18
N
NSS
H2N
OO
F3C
OOH
H
Column: (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (60/40)Ethanol/Hexane + 0.1%TriethylamineFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 32.0 mink'1 = 3.78α = 1.66reference 55
Column: (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (80/20)Hexane/IPA Flow Rate: 2.0 mL/minDetection: UV 254 nmRun Time: 32.0 mink'1 = 15.64α = 1.33reference 55
McN 5652 Bupivacaine
Cyclandelate
p-Chloro-Warfarin
Indapamide
Tolperisone
N
SCH3McN 56522% IPA/hex w. 0.2%
diethylamine1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 0.85α = 1.36reference 32
NN
O
H
Bupivacaine80:20:0.1 hexane/IPA/TEA1 ml/min; 254 nmRun Time = 7-8 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.89α = 1.25reference 18
H3C
O
CH3
N
Tolperisone99:1:0.1 hexane/IPA/TEA1 ml/min; 254 nmRun Time = 18 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.81α = 1.10reference 18
-chloro-warfarin
1 64
O O
OH
CH3
O
Cl
p-Chloro-Warfarin85:15:0.1 MeOH/H2O/HOAc1 ml/min; 254 nmRun Time = 12 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.64α = 1.93reference 18
Cyclandelate (mixture of isomers)hexane1 ml/min; 254 nmRun Time = 35 min4.6 mm x 25 cm
Whelk-O 1reference 18
OH
O
O
Iindapamidek'1 = 2.46α = 1.681:1 hexane/IPA1 ml/min; 220 nmRun Time = 14 min4.6 mm x 25 cm
Whelk-O 1reference 18 N
NH
O
CH3
S
Cl
NH2
OO
Column:(S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (60/40)
Ethanol/Hexane + 0.1%Triethylamine
Flow Rate: 1.0 mL/minDetection: UV 280 nmRun Time: 17.0 mink'1 = 3.78α = 1.14reference 56
Column = (R,R)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)Hexane/IPA Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 25.0 mink'1 = 3.45α = 2.04reference 53
62 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Miscel laneous Pharmaceut icals
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 63
Miscel laneous Pharmaceut icals REGISNicardipine Isradipine (reversed phase)
Hanessian’s Lignan
SC 41930
Tropicamide
Isradipine (normal phase)
U-94863U-100057
nicardipine
k' 6 06
N
H
H3C CH3
O OCH3
OO
NO2
N
H3C
Nicardipine73:27:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 30 min4.6 mm x 25 cm
Whelk-O 1k'1 = 6.06α = 1.52reference 18
N
H
H3C CH3
O OCH3
OO
NO
N
Isradipine (reversed phase)63/37 MeOH/H2O1 ml/min; 254 nmRun Time = 35 min4.6 mm x 25 cm
Whelk-O 1k'1 = 11.21α = 1.12reference 18
N
O
N
N
H
H3C CH3
O
O
O
O
H3C
Isradipine (normal phase)98:2:0.5 hexane/IPA/TEA1 ml/min; 254 nmRun Time = 52 min4.6 mm x 25 cm
Whelk-O 1k'1 = 9.71α = 1.10reference 18
SC 41930
k'1 = 1.05
H3C
O OCH3
O O
O
HO
HO
SC 4193080:20:0.5 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 6 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.05α = 1.12reference 7
Hanessian's lignanmethanol1 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm
Whelk-O 1k'1 = 0.94α = 1.69reference 7
O
OO
O
H
H
OCH3
OCH3H3CO
TropicamideColumn: (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase: (75/25)Hexane/Ethanol
Flow Rate: 1.5 mL/minDetection: UV 254 nmRun Time = 13.9 mink'1 = 4.52α = 1.49reference 46
O O
OH
U-10005765:35 hexane/IPA90 ml/min to 34 min,
then 120 ml/minRun Time = 50 min5.1 cm x 25 cm
Whelk-O 1Sample Load = 1.9 greference 37
N Cl
O
Cl
Cl
U-9486370:30:0.5 hexane/
IPA/HOAC12 ml/min; 254 nm2.1 cm x 25 cm
Whelk-O 1Run Time = 12 minSample Load = 40 mgreference 37
64 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
U-94863
ProglumideTemazepam
N Cl
O
Cl
Cl
U-9486340:60:0.5 hexane/IPA/HOAc1 ml/min; 254 nmrun time = 15 min4.6 mm x 25 cm
Whelk-O 1k'1 = 2.26α = 1.95reference 37
Column: (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (97/3)
Hexane/IPA +0.1% Acetic acid
Flow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 31.0 mink'1 = 12.05α = 1.34reference 46
N
O
H
N
O
OHO
Proglumide75:25:0.1 hexane/IPA/HOAc1 ml/min; 254 nmrun time = 10 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.54α = 1.49reference 18
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.61α = 1.48reference 44
N
N
O
H
CH3
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.66α = 1.69reference 44
N
N
O
H
CH3
N
N
O
H
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.29α = 1.83reference 44
N
N
O
H
CH3O2N
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.56α = 1.25reference 44
REGIS Miscel laneous Pharmaceut icals
TroglitazoneTroglitazoneColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (90/10)Hexane/IPA + 0.1% Acetic Acid
Flow Rate = 2.0 mL/minDetection = UV 220 nmk'1 = 13.05α = 1.22reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 65
Miscel laneous Pharmaceut icals REGIS
N
N
O
H
CH3Cl
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.38α = 1.44reference 44
N
N
O
HCl
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.34α = 1.60reference 44
N
N
O
H
F
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.29α = 1.83reference 44
N
N
O
H
Cl
Cl
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.34α = 1.78reference 44
N
N
O
H
Cl
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.37α = 1.90reference 44
N
N
O
H
F
Cl
30% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.18α = 1.72reference 44
70:30:05 hexane/2-propanol/diethyl amine1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.70α = 1.55reference 44
N N
N
O
H
CH3
70:30:05 hexane/2-propanol/diethyl amine1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 2.36α = 1.33reference 44 N N
N
O
H
F
66 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Miscel laneous Pharmaceut icals
N N
N
O
H
70:30:05 hexane/2-propanol/diethyl amine1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.90α = 1.45reference 44 N N
N
O
H
Cl
70:30:05 hexane/2-propanol/diethyl amine1 ml/min; 254 nm4.6 mm x 25 cm
Whelk-O 1k'1 = 1.73α = 1.59reference 44
H3CO
N
OCH3
O
N
N
40% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1α = 1.34Rs = 2.10reference 45
N
NH
NH
O
H
OCH3
50% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.32Rs = 2.10reference 45
N
OH
NH
HO
O O
10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1α = 1.29Rs = 2.10reference 45
N
O
NH
HO
O O
10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1α = 1.10Rs = 0.95reference 45
45% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1α = 1.57Rs = 2.20reference 45
NN
O
H
O
NH
Br
45% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 2.17Rs = 2.20reference 45 N
N
O
H
H
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 67
Miscel laneous Pharmaceut icals REGIS
NO
CH3
H
H
Cl10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.04Rs = 0.60reference 45
NO
CH3
H3C
H
Br10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.04Rs = 0.60reference 45
F
O
OCH3
15% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.13Rs = 1.50reference 45
NN
O
O
CH3O
NH
CH3
H2N
40% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.22Rs = 1.50reference 45
F3C N
O
H O
Cl
OCH3
O
10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.11Rs = 1.50reference 45
Bendroflumethiazide
ThalidomideIndapamide
Bendroflumethiazide Column = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (75/25) Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 18 mink'1 = 2.99α = 1.84reference 46
N
N
SS
H2N
OO OO
F3C
H
H
NN
H
CH3
O
Cl
SNH2
O O
IndapamideColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (75/25) Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 16 mink'1 = 3.09α = 1.58reference 46
ThalidomideColumn = (R,R)-ULMO 25 cm x 4.6 mmMobile Phase: (90/10)
Hexane/IPA + 0.1% Acetic acid
Flow Rate = 1.0 mL/minDetection = UV 220 nmRun Time = 28.0 mink'1 = 7.71α = 1.22reference 46
Warfarin Chlorthalidone
Flobufen and Flobufen Metabolites
4(3H)-Quinazolone Derivatives
Flobufen Metabolites
4(3H)-Quinazolone Derivatives4(3H)-Quinazolone Derivatives
68 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Miscel laneous Pharmaceut icals
α = 1.14
α = 1.14 α = 1.14
α = 1.20α = 1.08
WarfarinColumn: (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (70/30)
Heptane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 230 nmRun Time: 6.5 mink'1 = 0.89α = 1.36reference 48
ChlorthalidoneColumn = (S,S)-DACH-DNB
25 cm x 4.6 mmMobile Phase = (99/1)
CH2Cl2/CH3OH + 0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 20.0 mink'1 = 9.38α = 1.18reference 46
Flobufen MetabolitesColumn = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (97/3)
Heptane/Glyme + 0.1% TFA
Flow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 21.0 minreference 47
Flobufen and FlobufenMetabolites
Column = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (90/10)Heptane/IPA + 0.1% TFA Flow Rate = 2.0 mL/minDetection = UV 230 nmRun Time = 24.0 minreference 47
4(3H)-Quinazolone DerivativesColumn = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (80/20)
Hexane/EthanolFlow Rate = 1.0 mL/minDetection = UV 225 nmRun Time = 16.0 mink'1 = 2.88α = 1.56reference 58
4(3H)-quinazolonederivatives
Column = (S,S)-Whelk-O 125 cm x 4.6 mm
Mobile Phase = (80/20)Hexane/Ethanol
Flow Rate = 1.0 mL/minDetection = UV 225 nmRun Time = 17.0 mink'1 = 2.95α = 1.62reference 58
4(3H)-quinazolone derivativesColumn = (S,S)-
Whelk-O 125 cm x 4.6 mm
Mobile Phase = (90/10)Hexane/IPA
Flow Rate = 1.0 mL/minDetection = UV 225 nmRun Time = 15.0 mink'1 = 3.54α = 1.19reference 58
Dexmedetomidine (Enriched)Dexmedetomidine (Enriched)Column = (S,S)-Whelk-O 2
25 cm x 4.6 mmMobile Phase = (90/10)
Hexane/Ethanol + 10 mM Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 220 nmk'1 = 3.41α = 1.39reference 46
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Miscel laneous Pharmaceut icals REGIS
Sulpiride
Ketoconazole
Coumachlor
Tofisopam and it’s ConformersTofisopam and it’s ConformersColumn = (R,R)-β-Gem 1
25 cm x 4.6 mmMobile Phase = (70/30)
Hexane/Ethanol + 0.1% TEAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 25.0 mink'1 = 2.66α = 3.13reference 46
4(3H)-Quinazolone Derivatives 4(3H)-Quinazolone Derivatives
KetamineIfenprodil
4(3H)-Quinazolone DerivativesColumn = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (80/20)
Hexane/EthanolFlow Rate = 1.0 mL/minDetection = UV 225 nmRun Time = 21.0 mink'1 = 3.75α = 1.57reference 58
4(3H)-Quinazolone DerivativesColumn = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (80/20)
Hexane/EthanolFlow Rate = 1.0 mL/minDetection = UV 225 nmRun Time = 15.0 mink'1 = 3.19α = 1.37reference 58
IfenprodilColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (85/15)Hexane/IPA +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 220 nmRun Time = 16.5 mink'1 = 6.16α = 1.32reference 46
KetamineColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (99/1)Hexane/IPA + 0.1% TEA
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 22.0 mink'1 = 6.37α = 1.14reference 46
KetoconazoleColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (46/46/8)CH2Cl2/Hexane/IPA +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 16.0 mink'1 = 6.60α = 1.19reference 46
CoumachlorColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (65/35)
Hexane/Ethanol +0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 1.48α = 2.90reference 46
SulpirideColumn = (R,R)-DACH-DNB
25 cm x 4.6 mmMobile Phase = (95/5)
CH2Cl2/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 14.0 mink'1 = 5.92α = 1.24reference 46
70 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Miscel laneous Pharmaceut icals
Ofloxacin Isoxsuprine
Cromakalim
Warfarin (Reversed Phase)
Trichlormethiazide
Warfarin (Normal Phase)
PrilocaineTemazepam
OfloxacinColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (43/43/14)
CH2Cl2/Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 2.96α = 1.24reference 46
IsoxsuprineColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (95/5)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 2.0 mL/minDetection = UV 220 nmRun Time = 28.0 mink'1 = 17.91α = 1.08reference 46
Warfarin (normal phase)Column = (R,R)-
Whelk-O 125 cm x 4.6 mm
Mobile Phase = (65/35) Hexane/IPA+ 0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 11.5 mink'1 = 1.54α = 2.07reference 46
Warfarin (reversed phase)Column = (R,R)-
Whelk-O 125 cm x 4.6 mm
Mobile Phase = (70/30) CH3OH/H2O+ 0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 15.0 mink'1 = 3.54α = 1.55reference 46
CromakalimColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (92/8)
Hexane/EthanolFlow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 21.0 mink'1 = 9.18α = 1.14reference 46
TrichlormethiazideColumn = (R,R)-ULMO
25 cm x 4.6 mmMobile Phase =
(75/25)Hexane/IPA +0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 15.0 mink'1 = 5.16α = 1.43reference 46
TemazepamColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (80/20) Hexane/IPA + 0.1% Acetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 13.0 mink'1 = 6.86α = 1.34reference 46
PrilocaineColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase =
(99/1) Hexane/Ethanol + 0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 15.0 mink'1 = 5.70α = 1.28reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 71
Miscel laneous Pharmaceut icals REGISLorazepam Althiazide
Methadone Hydrochloride
Metolazone
Ethotoin
Clenbuterol
LansoprazoleZopiclone
LorazepamColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (70/30)
Hexane/IPA +0.1% Acetic Acid
Flow Rate = 1.5 mL/minDtection - UV 254 nmRun Time = 9.0 mink'1 = 2.08α = 2.02reference 46
AlthiazideColumn = (S,S)-ULMO
25 cm x 4.6 mmMobile Phase = (75/25)
Hexane/IPA +0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 13.0 mink'1 = 3.94α = 1.53reference 46
ClenbuterolColumn = (R)-α-Burke 2
25 cm x 4.6 mmMobile Phase = (90/10)
CH2Cl2/Ethanol +0.01 M AmmoniumAcetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 12.0 mink'1 = 4.99α = 1.09reference 46
MetolazoneColumn = (R,R)-
Whelk-O 125 cm x 4.6 mm
Mobile Phase = (55/45)Hexane/Ethanol
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 1.93α = 2.43reference 46
Methadone HydrochlorideColumn = (S)-α-Burke 2
25 cm x 4.6 mmMobile Phase =
(88/12)Hexane/Ethanol + 0.1% TEA
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 10.0 mink'1 = 3.50α = 1.34reference 46
EthotoinColumn = (S,S)-Whelk-O 1
25 cm x 4.6 mmMobile Phase =
(75/25)Hexane/Ethanol
Flow Rate = 1.5 mL/minDtection - UV 254 nmRun Time = 11.0 mink'1 = 1.65α = 3.03reference 46
ZopicloneColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (95/5)
CH2Cl2/Ethanol + 0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 1.94α = 2.01reference 46
LansoprazoleColumn = (S)-α-Burke 2
25 cm x 4.6 mmMobile Phase =
(94/3/3)CH2Cl2/Ethanol/Methanol + 0.2% Acetic AcidFlow Rate = 1.5 mL/min
Detection = UV 254 nmRun Time = 6.0 mink'1 = 0.88α = 2.43reference 46
Chlormezanone Tetrabenazine
trans-U-50488HDihydrotetrabenazine
72 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Miscel laneous Pharmaceut icals
ChlormezanoneColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (60/40)
Hexane/IPAFlow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 13.0 mink'1 = 4.48α = 1.36reference 46
TetrabenazineColumn = (S,S)-Whelk-O 1
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (55/45) Hexane/IPA + 0.1% TFA
Flow Rate = 1.5 mL/minDetection = UV 280 nmRun Time = 13.4 mink'1 = 3.35α = 1.93reference 46
DihydrotetrabenazineColumn = (S,S)-Whelk-O 1
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (60/40) Hexane/IPA + 0.1% TFA
Flow Rate = 1.5 mL/minDetection = UV 280 nmRun Time = 9.3 mink'1 = 2.50α = 1.65reference 46
trans-U-50488HColumn = (3R,4S)-Pirkle I-J
25 cm x 4.6 mmMobile Phase = (92/8)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 2.0 mL/minDetection = UV 220 nmRun Time = 12.0 mink'1 = 6.71α = 1.27reference 46
Fluridil Alfuzosin
PazufloxacinDoxazosin
FluridilColumn = (S,S)-Whelk-O 2
25 cm x 4.6 mmMobile Phase =
(57/43)H2O/CH3OH
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 12.9α = 1.18reference 46
AlfuzosinColumn = (R,R)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (68/28/4)Hexane/CH2Cl2/Ethanol + 4 mM Ammonium Acetate
Flow Rate = 2.0 mL/minDetection = UV 254 nmk'1 = 7.37α = 1.15reference 46
DoxazosinColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (66/29/5)
Hexane/CH2Cl2/Ethanol + 5 mM Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 14.2α = 1.13reference 46
PazufloxacinColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (40/40/20)
CH2Cl2/Hexane/IPA+ 0.15% TFA
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 6.7 mink'1 = 1.71α = 1.58reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 73
Miscel laneous Pharmaceut icals REGISMosapride Modafinil
Lorglumide
Nadifloxacin
Idazoxan
Sulindac
MosaprideColumn = (R,R)-
Whelk-O 110/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (66/28/6)Hexane/CH2Cl2/Ethanol
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 7.37α = 1.19reference 46
ModafinilColumn = (S,S)-Whelk-O 1
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (65/35)Hexane/IPA
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 3.57α = 1.75reference 46
SulindacColumn = (R,R)-Whelk-O 1
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (48/48/4)Hexane/CH2Cl2/IPA+ 0.1% Acetic acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 4.32α = 1.45reference 46
NadifloxacinColumn = (S,S)-Whelk-O 1
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (45/45/10)CH2Cl2/Hexane/IPA+ 10 mM Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 2.95α = 1.58reference 46
LorglumideColumn = (R,R)-Whelk-O 1
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (95/5)Hexane/IPA + 0.1% Acetic Acid
Flow Rate = 2.0 mL/minDetection = UV 254 nmk'1 = 5.22α = 1.25reference 46
IdazoxanColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (70/29/1)
Hexane/MethyleneChloride/IPA+ 0.1% TEA
Flow Rate = 2.0 mL/minDtection - UV 254 nmk'1 = 5.86α = 1.23reference 46
74 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
r-7,t-8-Dihydroxy-t-9, 10-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene
r-7,t-8-Dihydroxy-t-9, 10-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene
40% EtOH/Hexane4.6 mm x 25 cm (R,R) β-Gem 11 ml/min; 254 nmRun Time = 14 mink'1 = 3.18α = 1.25
O�H�
HO�
O�
1-Naphthylureaphenethylamine30% EtOH/Hexane4.6 mm x 25 cm
D-Phenyglycine1 ml/min; 254 nmRun Time = 10 mink'1 = 2.37α = 1.22
HN� C� N� CH�
CH�3�O� H�
Diol Epoxides REGIS Ureas REGIS1-Naphthylureaphenethylamine
Hexobarbital
N�
N� O�Na�
O�
CH�3�
H�3�C�
Hexobarbital5% EtOH/Hexane0.7 ml/min; 254nmrun time = 16 min4.6 mm x 25 cm
L-Leucinek'1 = 2.89α = 1.10
REGIS Barbi turates
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 75
Natural Products REGIS
Calanolide A (semi prep)Calanolide A
Flavanone 2-cis-4-trans-Abscisic Acid (ABA)
Combretastatin D-1
ABA Methyl Ester
Combretastatin D-1
2-trans-4-trans-Abscisic Acid
flavanone
k'1 = 7 08
O
OFlavanone1% IPA/hexane1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm
Whelk-O 1k'1 = 7.08α = 1.04reference 26 O
CH3
OH
CH3H3C
OHO
2-cis-4-trans-Abscisic Acid (ABA)80:20:0.5 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm
Whelk-O 1k'1 = 1.58α = 1.39reference 9
O
CH3
OH
CH3H3C
O
OH
2-trans-4-trans-AbscisicAcid (ABA)80:20:0.5
Hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm
Whelk-O 1k'1 = 2.08α = 1.21reference 9
O
CH3
OH
CH3H3C
O
OH
O O
CH3
ABA Methyl Ester80:20:0.5
Hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm
Whelk-O 1k'1 = 2.41α = 1.31reference 9
Combretastatin D-120% IPA/Hexane2 ml/min; 254 nmrun time = 13 min4.6 mm x 25 cm
Whelk-O 1k'1 = 4.54α = 1.45reference 17
O
OH
O
OO
Combretastatin D-1semi-prep separation20% IPA/hexane2 ml/min; 300 nm200 µl of 12.7 mg/ml solnload = 2.5 mgrun time = 10 min4.6 mm x 25 cm
Whelk-O 1reference 17
O
OH
O
OO
O O
O
OH
O
Calanolide A10% IPA/hexane1.25 ml/min; 270 nmrun time = 18 min4.6 mm x 25 cm
Whelk-O 1k'1 = 3.2α = 1.4reference 16
O O
O
OH
O
Calanolide A (semi prep)10% IPA/hexane1.25 ml/min; 270 nmrun time = 18 min4.6 mm x 25 cm
Whelk-O 15 mg samplek'1 = 3.2α = 1.4reference 16
Abscisic AcidAbscisic AcidColumn = (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase = (85/15)
Hexane/IPA +0.1% Acetic Acid
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.52α = 1.38reference 46
TetrahydropalmatineTetrahydropalmatineColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mm
Mobile Phase = (50/50)Hexane/IPA
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 6.66α = 1.46reference 46
76 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Natural Products
REGIS β−Blockers
LuciferinTaxifolinLuciferinColumn = L-Leucine
25 cm x 4.6 mmMobile Phase = (60/40)
Hexane/Ethanol + 0.04 mMAmmonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 15.5 mink'1 = 6.09α = 1.25reference 46
TaxifolinColumn = (S,S)-Whelk-O 2
10/100 (FEC)25 cm x 4.6 mm
Mobile Phase = (85/15)Hexane/Ethanol + 0.1% TFA
Flow Rate = 2.0 mL/minDetection = UV 220 nmk'1 = 11.87α = 1.20reference 46
β-Blockerβ-blockerColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (92/8)
CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 11.0 mink’1: 2.27α: 1.42reference 59
BambuterolBambuterolColumn = (R,R)-alpha-Burke 2
25 cm x 4.6 mmMobile Phase = (40/40/20)
Hexane/MethyleneChloride/Ethanol + 20 mMAmmonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmk'1 = 3.74α = 1.35reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 77
β−Blockers REGISAlprenolol Betaxolol
Bufuralol
Bupranolol
Metoprolol
Atenolol
β-BlockerTulobuterol HCI
O
OH
N
H
Alprenolol90:5:5 CH2C12/EtOH/MeOH10 mM NH4OAc1 ml/min; 254 nmrun time = 10 min4.6 mm x 25 cm
α-Burke 2k'1 = 1.44α = 1.44reference 33
O
OH
N
H
O
Betaxolol85:10:5 CH2C12/EtOH/MeOH10 mM NH4OAc1 ml/min; 254 nmrun time = 11 min4.6 mm x 25 cm
α-Burke 2k'1 = 2.36α = 1.25reference 33
O
H2N
O
OH
N
H
Atenolol85:10:5CH2C12/EtOH/MeOH15 mM NH4OAc1 ml/min; 254 nmrun time = 16 min4.6 mm x 25 cm
α-Burke 2k'1 = 4.41α = 1.13reference 33
BupranololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (85/15)
CH2Cl2/Ethanol + 0.015M Ammonium Acetate
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 8.5 mink’1: 1.44α: 1.47reference 46
BufuralolColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (90/10)
CH2Cl2/Ethanol + 0.02 M AmmoniumAcetate
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 7.0 mink’1: 0.91α: 2.01reference 46
metoprolol85:10:5 CH2C12/EtOH/MeOH10 mM NH4OAc1 ml/min; 254 nmrun time = 13 min4.6 mm x 25 cm
α-Burke 2k'1 = 2.66α = 1.28reference 33
O
OH
N
H
O
CH3
Tulobuterol HCIColumn: (S)-α-Burke 2
25 cm x 4.6 mmMobile Phase: (91/9)
CH2Cl2/Ethanol + 0.01 M Ammonium Acetate
Flow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 15.0 mink’1: 6.38α: 1.13reference 46
β-BlockerColumn: (S,S)-
DACH-DNB25 cm x 4.6 mmMobile Phase:
(90/10) CH2Cl2/IPA
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 18.0 mink'1: 4.52α: 1.29reference 59
78 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS β−Blockers
Nadolol Timolol Maleate
Carazolol
NadololColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (78/22)
Hexane/Ethanol +0.01 M Ammonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 270 nmRun Time = 9.5 mink'1 = 3.05α = 1.43reference 46
Timolol MaleateColumn = (3R,4S)-Pirkle 1-J
25 cm x 4.6 mmMobile Phase =
(94/3/3) CH2Cl2/Ethanol/IPA+ 0.01M Ammonium Acetate
Flow Rate = 1.0 mL/minDetection = UV 294 nmRun Time = 16.0 mink'1 = 3.72α = 1.33reference 46
CarazololColumn = (R)-α-Burke 2
25 cm x 4.6 mmMobile Phase =
(46/46/8) CH2Cl2/Methanol/Ethanol + 0.01 MAmmonium Acetate
Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 15.0 mink'1 = 6.73α = 1.10reference 46
Practolol
Pronethalol
Practolol85:10:5 CH2C12/
EtOH/MeOH15 mM NH4OAc1 ml/min; 254 nmrun time = 19 min4.6 mm x 25 cm
α-Burke 2k'1 = 4.78α = 1.14reference 33
OH
N
H
Pronethalol90:10 CH2C12/EtOH15 mM NH4OAc1 ml/min; 254 nmrun time = 15 min4.6 mm x 25 cm
α-Burke 2k'1 = 3.26α = 1.31reference 33
Pindolol
Oxprenolol
Propranolol
PindololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (80/20)
CH2Cl2/Ethanol + 0.04M Ammonium Acetate
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 11.0 mink’1: 1.56α: 2.06reference 46
OxprenololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (90/10)
CH2Cl2/Ethanol + 0.015M Ammonium Acetate
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 13.5 mink’1: 3.55α: 1.15reference 46
PropranololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (80/20)
CH2Cl2/Ethanol + 0.04M Ammonium Acetate
Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 6.5 mink’1: 0.80α: 1.80reference 46
practolol
O
OH
N
H
N
O
H
H3C
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Amino Acids REGISNorleucine 4-Fluorophenyalanine
1-Aminoindan
Arginine
Tyrosine
1,2,3,4-Tetrahydro-1-naphthylamine
LeucineMethionine
NorleucineColumn: ChiroSil® RCA(+)
or SCA(-)15 cm x 4.6 mm
Mobile Phase: (45/55) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 5.6 mink'1: 1.28α: 1.75
4-FluorophenyalanineColumn: ChiroSil® RCA(+) or
SCA(-) 15 cm x 4.6 mmMobile Phase: (70/30)
CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.5 mL/minDetection: UV 210 nmRun Time: 9.6 mink'1: 2.92α: 2.56
1,2,3,4-Tetrahydro-1-naphthylamineColumn: ChiroSil® RCA(+)
or SCA(-) 15 cm x 4.6 mmMobile Phase: (84/16)
CH3OH/H2O+10 mM H2SO4 and 0.1% TEA
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 3.5 mink'1: 0.82α: 1.76
ArginineColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (84/16) CH3OH/H2O+10 mM H2SO4
Flow Rate: 0.8 mL/minDetection: UV 210 nmRun Time: 4.9 mink'1: 1.21α: 1.64
1-AminoindanColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (84/16)CH3OH/H2O+5 mM HClO4
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 4.8 mink'1: 1.44α: 1.91
TyrosineColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (70/30) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.5 mL/minDetection: UV 210 nmRun Time: 9.1 mink'1: 2.95α: 2.38
MethionineColumn: ChiroSil® RCA(+)
or SCA(-) 15 cm x 4.6 mm
Mobile Phase: (45/55) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 7.5 mink'1: 1.64α: 2.04
LeucineColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (45/55) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 5.5 mink'1: 1.03α: 2.14
80 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS Amino Acids
KynurenineKynurenineColumn = (S,S)-Whelk-O 1
10/100 (FEC) 25 cm x 4.6 mmMobile Phase =
(65/35)H2O/CH3OH + 0.1% Acetic Acid
Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 9.0 mink'1 = 1.17α = 1.99reference 46
Serine
Tryptophan
Phenylalanine
NorvalinePhenylglycine
TryptophanColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (70/30) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.5 mL/minDetection: UV 210 nmRun Time: 11.0 mink'1: 4.06α: 2.15
SerineColumn: ChiroSil® RCA(+)
or SCA(-)15 cm x 4.6 mm
Mobile Phase: (84/16) CH3OH/H2O+5 mM HClO4
Flow Rate: 0.8 mL/minDetection: UV 210 nmRun Time: 6.0 mink'1: 1.37α: 1.99
PhenylalanineColumn: ChiroSil® RCA(+) or
SCA(-) 15 cm x 4.6 mmMobile Phase: (70/30)
CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.5 mL/minDetection: UV 210 nmRun Time: 8.9 mink'1: 2.66α: 2.57
PhenylglycineColumn: ChiroSil® RCA(+)
or SCA(-)15 cm x 4.6 mmMobile Phase: (70/30)
CH3OH/H2O+10 mM H2SO4 and 0.1% TEA
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 13.1 mink'1: 3.14α: 2.60
NorvalineColumn: ChiroSil® RCA(+) or
SCA(-)15 cm x 4.6 mmMobile Phase:
(45/55) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 5.3 mink'1: 1.15α: 1.79
D,L-p-Hydroxy-PhenylglycineD,L-p-Hydroxy-PhenylglycineColumn: ChiroSil®-SCA(+)
15 cm x 4.6 mmMobile Phase:
(50/50) CH3ON/H2O+0.02% Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 11.0 mink'1: 2.11α: 2.29reference 46
GlutamineGlutamineColumn: ChiroSil® SCA(-)
25 cm x 4.6 mmMobile Phase:
(65/35) CH3CN/H2O+0.01% Acetic acid
Flow Rate: 1.5 mL/minDetection: UV 210 nmRun Time: 6.5 mink'1: 1.51α: 1.61reference 46
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 81
Amino Acids REGISHistidine Glutamic Acid
Lysine
EthionineDOPA
HistidineColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (45/55) CH3OH/H2O+10 mM Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 26.0 mink'1: 10.96α: 1.27
Glutamic AcidColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (65/35) CH3OH/H2O+0.05% Phosphoric acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 4.5 mink'1: 0.71α: 2.27
DOPAColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (70/30) CH3OH/H2O+0.01% Phosphoric acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 5.5 mink'1: 0.97α: 2.30
EthionineColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (75/25) CH3OH/H2O+0.02% Acetic acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 6.2 mink'1: 1.29α: 2.07
LysineColumn: ChiroSil®
RCA(+) or SCA(-)15 cm x 4.6 mm
Mobile Phase: (70/30) CH3OH/H2O+0.01% Phosphoric acid
Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 5.3 mink'1: 1.44α: 1.48
Throughout the past 20 years, the Sales and Technical persons atRegis have fielded hundreds of different questions related to our
Chiral Stationary Phases (CSP’s). Listed here you will find some ofthe frequently asked questions. By no means is this a complete list,if you have questions regarding chiral chromatography, please feelfree to contact Regis directly or pass your question on through oneof our distributors.
What is the pressure rating of your columns?All analytical (25cm x 4.6 mm i.d.) and semi-preparative (25cm x 10.0 mm i.d.) columns manufactured by Regis can tolerate pressures up to 6000 psi. Larger columns will tolerate3000 psi. It is very important not to exceed the maximum pressurerating for any HPLC column as you may disrupt the integrity of thesilica bed and destroy the column.
Can Regis columns be reversed?Yes, all columns packed by Regis are fully reversible. In fact, Regiswas the first column manufacturer to sell a fully reversible HPLC column. It is recommended to reverse your column frequently. Thishelps keep the frit surface from becoming clogged with undissolvedsample or particulates in the mobile phase, thus extending the column life.
What is the pH range of your columns?All of Regis’ Chiral phases are bonded on silica. The recommendedpH range is 2.5 to 7.5. Limited usage outside of this pH range canbe tolerated, but it has been proven that extended usage outside ofthe range will decrease column life.
Can your columns be used in normal and reversed-phase solvents?Yes, all Pirkle-Type Chiral HPLC columns can be used in BOTHnormal and reversed-phase solvents. Generally, the Pirkle-TypeCSP’s will give better separations by using them with normal-phasesolvents. There are numerous examples, however; whereseparations with reversed-phase solvents will outperform those with normal-phase solvents.
Can I use the same column for reversed-phase and normal-phase solvent systems while doing method development?Yes, just make sure you completely flush out the column with a miscible solvent such as IPA or ethanol. We recommend at least 20 column volumes.
How long does it take your columns to equilibrate?The column should equilibrate after about 20 column volumes.When you are switching from normal to reversed-phase solventsystems and vise-versa, flush the column with a miscible solvent for20 column volumes. It should take another 20 column volumes toequilibrate. The equilibration volumes may vary depending on thecomposition of the mobile phase.
What type of silica do you use?Regis exclusively uses Exsil® for our 5-micron material andKromasil‚ for 10 and 16-micron material. Both brands of silica are100 angstrom in pore size.
Do you always need a modifier in the mobile phase?No modifiers are usually needed for initial method development.Modifiers can be used to improve peak shape and resolution whenthe samples are extremely basic or acidic in nature. Acetic acid orammonium acetate are recommended for acidic compounds, andtriethylamine, diethylamine or ammonium acetate arerecommended for basic compounds. Usually 0.1% of modifier is allthat is required. Note: Although TFA may be used as a modifier,its use should be limited. Acetic acid usually works as well as TFA.
Can I use your columns for SMB chromatography and SFC?Yes, many analytical and preparative chromatographers usePirkle-Type Chiral columns in both SFC and SMB. Specialhardware is necessary for certain column dimensions.
What is the difference between Whelk-O 1 and Whelk-O 2?Although the Whelk-O 1 and Whelk-O 2 both share the sameChiral selector, they have distinct differences. The Whelk-O 1 ismonofunctionally bonded to silica and the Whelk-O 2 istrifunctionally bonded. The Whelk-O 2 was designed to toleratestrong acidic modifiers such as TFA. The Whelk-O 2 was designedfor preparative use and is not available on 5-micron silica. Due tothe fact the Whelk-O 2 is a trifunctional bond, coverage on the silicawill be less than with Whelk-O 1. This decrease in the actual numberof bonded sites will decrease selectivity and not allow for exactreproducibility of a method developed on a Whelk-O 1 column.
Does my compound need an aromatic ring to achieve separation on a Pirkle-Type Chiral column?In most cases (not all), yes. Chiral recognition occurs at bindingsites. The potential π-π interaction that can occur between the aromatic rings on the Chiral selector and the aromatic ring on thesample is a major factor in achieving selectivity. Binding doesoccur at other sites such as acidic sites, basic sites and stericinteraction sites—this is why you do not always need a ring—butby far, the π-π interaction is the major binding site.
Can I use the Pirkle-Type Chiral columns in polar organic mode?Yes, even though the success rate is very poor, you can use thecolumns in polar organic mode. We do not recommend dedicatinga slot in your method development station for a Pirkle-Type Chiralcolumn if you are exclusively running in polar organic mode. Addanother Pirkle-Type column to your normal-phase system toachieve a higher success rate.
What sampling loading can I expect from Pirkle-Type ChiralHPLC columns?The typical loading range – with relative retention’s (alpha) greaterthan 1.3—is ~ 4-16 mg of sample per gram of packing. Below aretypical loadings for some of the different column sizes: Note:Factors, such as solubility, will greatly affect loading capacity.Analytical column, 25cm x 4.6mm, ~ 3.5 grams of packing,
loading is 14-56 mg/ injection.Semi-prep column, 25cm x 10.0mm, ~ 16 grams of packing,
loading is 64-256 mg/ injection.Prep column, 25cm x 21.1mm, ~ 72.5 grams of packing,
loading is 288-1,152 mg/ injection.
Frequently Asked QuestionsABOUT PIRKLE-TYPE CHIRAL STATIONARY PHASES AND COLUMNS FROM REGIS
82 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
STEP 1: Choosing the Appropriate Column:
We recommend using the following sequence of columns to startyour method development. When doing method development atRegis, the Whelk-O is our first choice as it exhibits the broadestdegree of generality.
Order of Preference:
� Whelk-O
� ULMO
� DACH-DNB
� α-Burke
� β-Gem
� Pirkle 1-J
� Leucine
� Phenylglycine
STEP 2: Choosing the Mobile Phase:
Certain factors such as solubility and future considerations forpreparative work usually help to determine whether to performyou method development with reversed-phase or normal phasesolvents. Pirkle-Type phases can be used in both modes, buttypically performs the best with normal phase solvents. Since themajority of analytical Chiral methods move on to preparativeseparations, we recommend using normal phase solvents.
Typical Mobile Phase Combinations:
� Hexane/IPA � Heptane/IPA
� Hexane/Ethanol � Methanol/H2O
� Hexane/CH2CL2/Ethanol � Ethanol/H2O
� Hexane/Ethyl Acetate � Acetonitrile/H2O
� Heptane/Ethanol � Methanol/CH2CL2
� Heptane/CH2CL2 � THF/H2O
� Hexane/CH2CL2 � Ethanol/CH2CL2
STEP 3: Start with a high percentage (~50%) ofstrong solvent (ethanol, IPA, ect.):
Starting with a strong solvent system ensures that all peaks willelute off the column quickly.
� If you achieve any resolution, (such as the above sample)move on to STEP 4.
� If your sample comes off in the void, decrease the strongsolvent by half.
� If your sample is now out of the void and you haveresolution, move on to STEP 4.
� If your sample is out of the void, and there is no resolution,change the column.
Quick Scheme Method DevelopmentFOR THE REGIS PIRKLE-TYPE CHIRAL STATIONARY PHASES
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 83
Steps 4 and 5 continued on pages 84 & 85
Sample: NaproxenColumn: (R,R)-Whelk-O 1
25 cm x 4.6 mmMobile Phase: (50/50)
Hexane/EthanolFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 6.5 min
84 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
STEP 4: Add a Mobile Phase Modifier (usually ~ 0.1%)
� For this sample, you can stop at 50/50 Hexane/Ethanol + 0.1% acetic acid if you are only looking for a basic methodor you can carry it forward to STEP 5 and optimize.
Quick Scheme Method DevelopmentFOR THE REGIS PIRKLE-TYPE CHIRAL STATIONARY PHASES
Recapping The First Four Steps:
As you can see, the peak shape of the initial separation is verypoor. To rectify this problem, a modifier is usually added. If youare satisfied with the peak shape—you do not need to add amodifier—move on to STEP 5 and optimize your separation.
� For basic or amine groups—add triethylamine, diethylamineor ammonium acetate
� For acidic groups—add acetic acid, trifluoroacetic acid orammonium acetate
� Although resolution increased with the addition of 0.1% of triethylamine to the mobile phase, the peak shape is stillvery poor.
� Try adding a different modifier
� Resolution and peak shape are excellent with the addition of0.1% of acetic acid
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral 85
STEP 5: Optimizing your method:
Quick Scheme Method DevelopmentFOR THE REGIS PIRKLE-TYPE CHIRAL STATIONARY PHASES
Optimizing a Chiral method is very similar tooptimizing an achiral method. Changing mobilephase component concentrations and even thecomponents themselves can dramatically changeresolution.
Increase the concentration of the weaker solvent:
� Increasing the hexane content increased the resolution in this example. Again, you can stop here and accept this asoptimized or continue on.
Change the strong solvent:
� By substituting IPA for ethanol, an increase in both resolution and alpha were achieved.
Optimization of a Chiral method can be assimple or as complicated as you want it to be.Different mobile phase components can be used; modifiers can be changed or eliminated;you can switch to reversed-phase solvents; you can change columns. The possibilities areendless. We suggest you keep it as simple as possible. Once you have achieved anacceptable separation, move on to the nextproject. Small increases in resolution and alpha are usually not worth the time spent in method development to achieve thoseincreases.
?Not sure which chiral column to use for your separation?Let the professional staff at Regis assist you with its free chiral screening service.
Simply fill out the chiral screening data sheet (see page 91 of this Guide) and pre-fax it to Regis or send it along with your sample of interest.
STRICTLY CONFIDENTIAL • FAST TURN AROUND TIME • NO OBLIGATION TO THE [email protected]
1. Pirkle, W. H.; Welch, C. J.; Burke, J. A., Lamm, B., Target-directed Design ofChiral Stationary Phases, Analytical Proceedings, 1992, 29, 225.
2. Pirkle, W. H.; Welch, C. J.; Hyun, M. H., Concerning the Role of Face-to-Edge π-π Interactions in Chiral Recognition, J. Chromatogr., 1992, 607, 126.
3. Pirkle, W. H.; Welch, C. J.; Lamm, B., Design, Synthesis, and Evaluation of anImproved Enantioselective Naproxen Selector, J. Org. Chem., 1992, 57, 3854.
4. Pirkle, W. H.; Welch, C. J., An Improved Chiral Stationary Phase for theChromatographic Separation of Underivatized Naproxen Enantiomers, J. Liq.Chromatogr., 1992, 15(11), 1947.
5. Pirkle, W. H.; Welch, C. J.; Wilson, S. R., Assignment of Absolute Configurationto an Improved Enantioselective Naproxen Selector, Chirality, 1994, 6, 615.
6. Welch, C. J., Analytical & Semipreparative Separation of Enantiomers Using theWhelk-O 1 Chiral Stationary Phase: Naproxen & Abscisic Acid as Case Studies,Chemistry in New Zealand, 1993, July, 9.
7. Pirkle, W. H.; Welch, C. J., Use of Simultaneous Face to Face to Edge π-π Interactions to Facilitate Chiral Recognition, Tetrahedron: Asymmetry, 1994, 5, 777.
8. Wilson, S. R.; Wu, Y.; Kaprinidis, N. A.; Schuster, D. I.; Welch, C. J., Resolutionof Enantiomers of C60-Enone Photoadducts: Mirror Image Fullerenes, J. Org.Chem., 1993, 58, 6548.
9. Welch, C. J., An Improved Method for the Direct Chromatographic Resolution ofAbscisic Acid Enantiomers, Chirality, 1993, 5, 569.
10. Pirkle, W. H.; Welch, C. J.; Zych, A. J., Chromatographic Investigation of theSlowly Interconverting Atropisomers of Hindered Naphthamides, J. Chromatogr.,1993, 648,101.
11. Zhen, L.; Conser, K. R.; Jacobsen, E. N., Asymmetric Alkene Aziridination withReadily Available Chiral Diimine-Based Catalysts, J. Amer. Chem. Soc., 1993,115, 5326.
12. Blum, A. M.; Lynam, K. G.; Nicolas, E. C., Use of a New Pirkle-type ChiralStationary Phase in Analytical and Preparative Subcritical Fluid Chromatographyof Pharmaceutical Compounds, Chirality, 1994, 6, 302.
13. Zhang, Y.; Schuster, G. B. A Search for Photoresolvable Mesogens: Synthesis andProperties of a Series of Liquid Crystalline, Axially Chiral 1-Benzylidene-4 -
[4'-[(p - alkylphenyl)ethnyl]phenyl]cyclohexanes, J. Org. Chem., 1994, 59, 1855.14. Pirkle, W. H.; Welch, C. J., Chromtographic and 1H NMR support for a
proposed chiral recognition model, J. Chromatogr., 1994, 683, 347.15. Wan, K. T.; Davis, M. E., Asymmetric Synthesis of Naproxen by Supported
Aqueous-Phase Catalysis, Journal of Catalysis, 1994, 148, 1.16. Cardellina, J.H.; Bokesch, H.R.; McKee, J.C.; Boyd, M.R., Resolution and
Comparative Anti-HIV Evaluation of the Enantiomers of Calanolides A and B,Bioorg & Med. Chem. Lett., 1995, 1011.
17. Rychnovsky, Pettit & Welch, unpublished results.18. Welch, Szczerba & Perrin, Regis Technologies, Inc., unpublished results.19. Pickard, S.T.; Pirkle, W.H.; Tabatabai, M.; Vogt, W.; Boehmer, V., Dissymmetric
Calix[4]arenes: Optical Resolution of Some Conformationally Fixed Derivatives,Chirality, 1993, 5, 310.
20. Villani, C.; Pirkle, W.H., Direct High-Performance Liquid ChromatographicResolution of Planar Chiral Tricarbonyl (h6-arene)-chromium(0) Complexes, J. Chromatogr., 1995, 693, 63.
21. Villani, C.; Pirkle, W.H., Chromatographic Resolution of the InterconvertingStereoisomers of Hindered Sulfinyl and Sulfonyl Naphthalene Derivatives,Tetrahedron: Asymmetry, 1995, 6, 27-30.
22. Casarini, D.; Lunazzi, L.; Alcaro, S.; Gasparrini, F.; Villani, C., Atropisomerism inHindered Naphthyl Sulfones Investigated by Dynamic NMR and Dynamic HPLCTechniques, J. Org. Chem., 1995, 60, 5515.
23. Hamper, B.C.; Dukesherer, D.R.; Moedritzer, K., Analytical and PreparativeSeparation of the Enantiomers of Pyrazole Phenyle Ether Herbicides on ThreeChiral Stationary Phases., J. Chrom., 1994, 666, 479-484.
24. Suarez, M.; Schuster, G.B., Photoresolution of an Axially ChiralBicyclo[3.3.0]octan-3-one: Phototriggers for a Liquid-Crystal-Based Optical Switch,J. Amer. Chem. Soc., 1995, 117, 6732.
25. Lalonde, J.J.; Govardhan, C.; Khalaf, N.; Martinez, A.G.; Visuri, K.; Margolin,A.L., Cross-linked Crystals of Candida Rugosa Lipase: Highly Effiecient Catalystfor the Resolution of Chiral Esters, J. Amer. Chem. Soc., 1995, 117, 6845.
26. Welch, C.J.; Perrin, S.R., The Whelk-O 1 Chiral Stationary Phase: Some RecentDevelopments, Poster presented at the 4th International Symposium on ChiralDiscrimination, Sept. 22, 1993, Montréal.
27. Stringham, R.W., Relationship Between Resolution and Analysis Time in ChiralSubcritical Fluid Chromatography, Chirality, 1996, 8, 249-257.
28. Courtesy of Suzanne Leung, Department of Pharmaceutics, University ofMinnesota.
29. Courtesy of Dhimant Desai, American Health Foundation.30. Courtesy of Hal Butler, Sepracor, Inc.31. Courtesy of Allan Rettie, Department of Medicinal Chemistry, University of
Washington.32. Courtesy of Chet Mathis, Department of Radiology, University of Pittsburgh
School of Medicine.33. Welch, C.J.; Perrin. S.R., Improved Chiral Stationary Phase for ß-blocker
Enantioseparations, J. Chromatogr., 1995, 690, 218.34. Pirkle, W.H.; Burke, J.A., Preparation of a Chiral Stationary Phase from an
α-amino Phosphonate, Chirality, 1989, 1, 57.35. Pirkle, W.H.; Burke, J.A., Chiral Stationary Phase Designed for β-blockers,
J. Chromatogr., 1991, 557, 173,.36. Perrin, S.R., “Fast Liquid Chromatography for the Analysis of Enantiomers” In
Pharmaceutical and Biomedical Applications of Liquid Chromatography; Riley,M., Lough, W.J., Wainer, Eds.; Pergamon Division of Elsevier Science Ltd.:Oxford, 1994; Vol. 1, Chapter 3.
37. Courtesy of Les Dolak, Department of Chemical & Biological Screening,Pharmacia & Upjohn, Inc.
38. Pirkle, W.H.; Gan, K.Z.; Brice, L.J., The Enhancement of Enantioselectivity byHalogen Substitutes, Tetrahedron: Asymmetry, 1996, 7, 2813-2816.
39. Pirkle, W.H.; Gan, K.Z., in press, 1997.40. Pirkle, W.H.; Brice, L.J.; Caccamese, S.; Principato, G.; Failla, S.,
J. Chromatogr., 1996, 721, 241-246.41. Pirkle, W.H.; Koscho, M.E.; Wu, Z., High-Performance Liquid Chromatographic
Separation of the Enantiomers of N-Aryloxazolinones, N-aryl Thiazolinones andtheir Sulfur Derivatives on a Synthetic Chiral Stationary Phase, J. Chromatogr.,1996, 726, 91-97.
42. Pirkle, W.H.; Koscho, M.E., J. Chrom, in press, 1997.43. Szczerba & Welch, Regis Technologies, Inc., unpublished results.44. Caccamese, S., Tetrahedron: Asymetry, 1996, 7, 2577-2584.45. Kennedy, J.K., Comparison of Chiral Separations on Polysaccharide Chiral
Stationary Phases to an Improved Pirkle Phase, J. Chromatogr., 1996, 725, 219-224.
46. Szczerba, T. J., Regis Technologies, Inc., unpublished results.47. Uray, G.; Kosjek, B., Simultaneous Enantioseparation of Flobufen and its
Diastereomeric Metabolites on a Pirkle Type Chiral Stationary Phase, Poster presented at the 11th International Symposium on Chiral Discrimination, July 25, 1999, Chicago.
48. Courtesy of Georg Uray, Karl Franzens University, Austria; Norbert Maier,University of Vienna, Austria; Wolfgang Lindner, University of Vienna, Austria.
49. Pirkle, W.H.; Lee, W.; Welch, C.J., Enantiomer, 1997, 2, 423-431.50. Pirkle, W.H.; Lee, W., Bull. Kor. Chem. Soc., 1998, 19(11), 1277-1280.51. Lee, W., Bull. Kor. Chem. Soc., 1998, 19(7), 715-717.52. Hyun, M.H.; Jin, J.S.; Lee, W., Bull. Kor. Chem. Soc., 1997, 18(3), 336-339.53. Kim, S.W.; Ahn, S.Y.; Koh, J.S.; Lee, J.H.; and Cho, H.Y., Tetrahedron Letters,
1997, 38(26), 4603-4606.54. Lee, W.; Kim, B.H, J. Of High Resolution Chromatogr., 1998, 21(3), 189-192.55. Courtesy of Wonjae Lee, LG Chemicals, Korea.56. Lee, J.Y.; Lee, Y.S.; Chung, B.Y.; Park, H., Tetrahedron, 1997, 53(7), 2449-
2458.57. Lee Wonjae, Analytical Lett., 1997, 30(15), 2791-2799.58. K. Gyimesi-Forras, Gy. Szasz, M. Szabo and J. Kokosi: Chiral liquid
chromatographic separation of new potential cholecystokinin antagonist nitrogen-containing heterocycles, Poster presented at the 12th International Symposium onChiral Discrimination, Sept. 24, 2000, Chamonix.
59. Courtesy of Dr. Francesco Gasparrini, Misiti,Villani, et al,; Rome University “La Sapienza.”
60. Courtesy of Georg Uray, Karl Franzens University, Austria.
REFERENCES
NOTESIf you have published literature or intend to publish literature referencing anyof Regis’ columns (Pirkle-types or others), we would appreciate a copy for ourfiles. Please send it directly to Regis (address at right).Regis would appreciate the opportunity of obtaining your permission to reference your material in our Application Guides. Please let us know if youhave application information you would like included in our future guides.PLEASE CONTACT REGIS FOR MORE INFORMATION.
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website: www.registech.com86 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 87
INDEX OF APPLICATION BY COMPOUND
Aryl Propionic Acid Non SteroidalAnti-Inflammatory Drugs (NSAIDS)..................................8-11
α-Trityl-2-naphthalenePropionic Acid.....................10
2-(4-Hydroxy-Phenoxy)Propionic Acid.....................10
3,5-Dimethylanilide-R,S-Ibuprofen ............................10
Carprofen...............................11Cicloprofen............................8,9Etodolac...................................8Fenoprofen ...............................8Flurbiprofen ..............................9Hydratropic Acid.....................11Ibuprofen..................................9Indoprofen..............................10Ketoprofen................................8Ketoprofen as 1-naphthylamide...8Loxoprofen ...............................9Naproxen (normal phase) .....9,10Naproxen (reversed phase) ........9Naproxen (semi prep)................8Naproxen Diisopropyl Amide .....9Naproxen Dimethyl Amide .......10Naproxen Methyl Amide..........10Naproxen Methyl Ester ............10Pirprofen ..................................8Rebamipide ............................10Tiaprofenic Acid........................8
Other Carboxylic Acids ..........11-15α-Methoxyphenyl Acetic Acid ...131,1’-Binaphthyl-2,2’-
Diylhydrogen Phosphate .......121-Cyclohexyl-1-phenylacetic
Acid ...................................141-Cyclopentyl-1-phenylacetic
Acid ...................................142-(2-Chloro-4-methylphenoxy)
Propionic Acid.....................142-(3-Chlorophenoxy)
Propionic Acid.....................142-Phenylcyclopropane
Carboxylate ........................122,3-Dibenzoyl-Tartaric Acid ......154-Chloromandelic Acid ............134-(Trifluoromethyl)-
Mandelic Acid.....................15Calcium Channel Blocker .........12Ditoluoyltartaric Acid ...............14Ketorolac................................13Mandelic Acid ........................12Phenylbutyric Acid...................11Phenylsuccinic Acid .................13Suprofen ................................14Tetrahydropyrimidine
Carboxylic Acid...................11Trolox ....................................12Trolox-methylether ...................14Vanilmandelic Acid .................14
Basic Amine ................................15Trans-11,12-Diamino-
9,10-dihydro-9,10-ethanoanthracene ................15
Basic Nitrogen ............................15Troger’s Base..........................15
Esters, Lactones, Ketones, Anhydrides ............................16-19
1’-Acetoxychavicol Acetate.......191,3,5-Triphenylpent-4-yn-1-one ..182-Methyl-1-Indanone ................162-Methyl-1-Tetralone.................183-Methyl-1-Indanone ................17Buckminsterfullerene-Enone
[2+2] Photoadducts..............19Diperodon ..............................18DPHB.....................................17Ethyl-2-(p-Hydroxyphenoxy)
Propionate ..........................19Methyl Mandelate ...................16Tert-butyl-2(benzamido)
cyclopentyl carbamate..........19
Amides, Imides, Carbamates, etc. ....................20-24
β-Lactam.................................24BOC-Ala ................................20CBZ Nornicotine .....................20CBZ-Phe .................................20CBZ-Val..................................20Cyclopentyl Benzoyl-diamide ....24EEDQ ....................................20
Epoxides .....................................24m-Cl-Styrene Oxide..................24Stilbene Oxide........................24Styrene Oxide.........................24
Alcohols.................................25-31α-Naphthyl Methyl Carbinol .....25β-Naphthyl Methyl Carbinol .....261,1’-Bi-2-Naphthol ...................261,1’-Binaphthol
Monomethylether ................281,1,2,-Triphenyl-1,
2-Ethanediol ........................271,2,3,4-Tetrahydro-1-Naphtol ...251-(4-Benzyloxy) Phenyl Ethanol..301-(4-Hydroxyphenyl) Ethanol .....291-(4-Methoxyphenyl)-
2-butanol ............................291-(4-Methoxyphenyl)-
2-propanol ..........................291-[(4-Phenyl) Phenyl] Ethanol .....301-(m-Chlorophenyl) Ethanol .......311-(m-Methylphenyl) Ethanol .......301-(m-Trifluoromethylphenyl)
Ethanol ...............................301-Naphthyl-2-Butanol ...............26
1-(o-Chlorophenyl) Ethanol........311-(o-Methoxyphenyl) Ethanol .....291-(o-Methylphenyl) Ethanol........301-(p-Bromophenyl) Ethanol ........301-(p-Fluorophenyl) Ethanol ........301-(p-Chlorophenyl) Ethanol .......311-(p-Methylphenyl) Ethanol........291-Phenylpentanol .....................271-Phenyl-2-propanol .................292-Methoxyphenyl Phenyl
Carbinol .............................282-Naphthyl-2-Butanol ...............262-Thiopheneethanol .................293-Thiopheneethanol .................299-Anthryl Trifluoromethyl
Carbinol .............................259-Anthrylethanol ......................26Acenaphthenol........................25Ibuprofenol .............................25Methyl 3-Phenyl-3azido-
2hydroxypropanoate (Erythro-diastereomer) ...........29
Phenyl Cyclohexyl Carbinol ......28Phenyl Ethyl Carbinol...............27Phenylethylene Glycol ..............31Phenyl Isopropyl Carbinol ........28Phenyl Methyl Carbinol ............27Phenyl Phenylethyl Carbinol......28Phenyl Propyl Carbinol.............27Phenyl Tribromomethyl
Carbinol .............................27Propafenone ...........................28Ranolazine .............................31Terfenedine.............................28Tert Butyl Phenyl Carbinol ........25Tetrahydrobenzopyrene-7-ol .....26Trans Phenyl Cyclohexanol
(Analytical vs. Preparative Run) ..................28
Diols, Hydroxyketones, etc. ........32Anisoin ..................................32Benzoin..................................32Hydrobenzoin.........................32Ipsdienol ................................32
Sulfoxides..............................33-35Omeprazole ...........................34Pantoprazole ..........................35Sulfinpyrazone........................34
Phosphorous Compounds .......36-38Cyclophosphamide..................36Phosphine Selenium Oxide .......37Secondary Phosphine
Oxide............................37,38Tertiary Phosphine Oxide ....37,38
Atropisomers .........................39-46Adam’s Acid Diethylamide .......46Amlodipine.............................46
Nimodipine ............................46Sulfone Atropisomer ................41Sulfoxide Atropisomer..............41Vapol.....................................46
Optical Switches, Liquid Crystal Components, etc. .............47
Mesogens...............................47Phototriggers...........................47
Allenes ..................................48-52
Organometallic Compounds ...53-55
Agricultural Compounds .........56-60Bromacil.................................56Chlorflurecol Methyl ................58Chrysanthemic Acid-
Ethyl Ester ...........................57Cis:trans Cypermethrin.............59Crotoxyphos ...........................58Devrinol, Napropamide ...........58Diclofop Methyl.......................58Dinocap .................................60Fenvalerate.............................60Fenoxaprop-ethyl.....................60Fluazifop-butyl.........................60Haloxyfop-ethoxyethyl ..............60Leptophos, Phosvel ..................57Mecoprop ..............................57Mecoprop Methyl ...................56Metalaxyl ...............................57Metolachlor ............................57Omite ....................................57Permethrin ..............................56PPO Inhibitors ...............56,58,59Propiconazole, Tilt...................58Quizalofop-ethyl......................60Resmethrin..............................57Sethoxydim.............................57Silvex Methyl ..........................59Tetramethrin............................56Tetramisole .............................59
Miscellaneous Pharmaceuticals61-73Alfuzosin ................................72Althiazide...............................71Bendroflumethiazide ...........61,67Bupivacaine............................62Chlormezanone.......................72Chlorthalidone ........................68Clenbuterol.............................71Coumachlor............................69Cromakalim............................70Cyclandelate ..........................62Cyclothiazide..........................61Dexmedetomidine....................68Dihydrotetrabenazine ..............72Doxazosin ..............................72Ethotoin..................................71Flobufen .................................68
Index of Application by Compound continued on page 88
88 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
Flobufen Metabolites................68Fluridil....................................72Hanessian’s Lignan .................63Idazoxan................................73Ifenprodil................................69Indapamide .......................62,67Isoxsuprine .............................70Isradipine (normal phase).........63Isradipine (reversed phase).......63Ketamine................................69Ketoconazole..........................69Lansoprazole ..........................71Lorazepam .............................71Lorglumide..............................73McN 5652.............................62Mephenytoin...........................61Metolazone ............................71Methadone Hydrochloride........71Modafinil ...............................73Mosapride..............................73Nadifloxacin...........................73Nicardipine ............................63Nirvanol.................................61Ofloxacin ...............................70Oxazepam .............................61p-Chloro-Warfarin ...................62Pantoprazole ..........................35Pazufloxacin ...........................72Prilocaine ...............................70Proglumide .............................64Quinazolone Derivatives .....68,69SC 41930..............................63Sulindac.................................73Sulpiride ................................69Temazepam.......................64,70Tetrabenazine.........................72Thalidomide.......................61,67Tofisopam and it’s
Conformers .........................69Tolperisone.............................62Trans-U-50488H......................72Trichlormethiazide ...................70Troglitazone ...........................64Tropicamide ...........................63U-100057 ..............................63U-94863 (analytical) ...............64U-94863 (preparative) .............63Warfarin (normal phase).....68,70Warfarin (reversed phase)........70Zopiclone ...............................71
Barbiturates ................................74Hexobarbital...........................74
Ureas..........................................741-Naphthylureaphenethylamine.74
Diol Epoxides ..............................74r-7,t-8-Dihydroxy-t-9,10-epoxy-
7,8,9,10-tetrahydrobenzo[a]pyrene ............................73
Natural Products ....................75-76
2-cis-4-trans-Abscisic Acid.........752-trans-4-trans-Abscisic Acid......75Abscisic Acid..........................76Abscisic Acid Methyl Ester........75Calanolide A ..........................75Combretastatin D-1..................75Flavanone ..............................75Luciferin .................................76Taxifolin .................................76Tetrahydropalmatine ................76
ß-Blockers..............................76-78Alprenolol ..............................77Atenolol .................................77Bambuterol .............................76Betaxolol ................................77Bufuralol.................................77Bupranolol..............................77Carazolol ...............................78Metoprolol..............................77Nadolol .................................78Oxprenolol .............................78Pindolol..................................78Practolol .................................78Pronethalol .............................78Propranolol.............................78Timolol Maleate ......................78Tulobuterol HCL.......................77
Amino Acids ..........................79-811-Aminoindan .........................791,2,3,4-Tetrahydro-1-
naphthylamine .....................794-Fluorophenylalanine..............79Arginine.................................79DOPA ....................................81Ethionine ................................81Glutamic Acid.........................81Glutamine ..............................80Histidine.................................81p-Hydroxy-Phenylglycine...........80Kynurenine .............................80Leucine...................................79Lysine.....................................81Methionine .............................79Norleucine .............................79Norvaline ...............................80Phenylalanine .........................80Phenylglycine..........................80Serine ....................................80Tryptophan .............................80Tyrosine .................................79
INDEX OF APPLICATION BY COMPOUND continued from page 87
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 89
INDEX OF APPLICATION BY COLUMN TYPE
α-Burke .......................................2Alprenolol..............................77Atenolol.................................77Bambuterol ............................76Betaxolol ...............................77Carazolol ..............................78Clenbuterol ............................71Diperodon .............................18Lansoprazole..........................71Methadone Hydrochloride .......71Metoprolol .............................77Omeprazole ..........................34Pantoprazole..........................35Practolol ................................78Pronethalol.............................78Tulobuterol HCL......................77
ChiroSil® RCA(+) and SCA(-)1-Aminoindan ........................791,2,3,4-Tetrahydro-1-naphthylamine........................794-Fluorophenylalanine .............79Arginine ................................79DOPA ...................................81Ethionine ...............................81Glutamic Acid ........................81Glutamine..............................80Histidine ................................81p-Hydroxy-Phenylglycine ..........80Leucine..................................79Lysine....................................81Methionine.............................79Norleucine.............................79Norvaline ..............................80Phenylalanine.........................80Phenylglycine .........................80Serine ...................................80trans-11,12-Diamino-9,10-
dihydro-9,10-ethanoanthracene................15
Tryptophan ............................80Tyrosine.................................79
DACH-DNBβ-Blockers .........................76,77β-Lactam................................24Chlorthalidone .......................68Fenoxaprop-ethyl ....................60Fluazifop-butyl ........................60Haloxyfop-ethoxyethyl .............60Phosphine Selenium Oxide ......37Quizalofop-ethyl .....................60Secondary Phosphine
Oxide ...........................37,38Sulfoxides ..............................34Sulpiride................................69Tertiary Phosphine Oxide ...37,38
ß-GEM 1r-7,t-8-Dihydroxy-t-9,10-epoxy-
7,8,9,10-tetrahydrobenzo[a]pyrene ...........................74
Tofisopam and it’s Conformers .69
LeucineHexobarbital ..........................74Luciferin.................................76
Phenylglycine1-Naphthylureaphenethylamine 74
Pirkle 1-J3,5-Dimethylanalide-R,S-
Ibuprofen............................10Adam’s Acid Diethylamide ......46Bufuralol ................................77Bupranolol .............................77Cis:trans Cypermethrin ............59Oxprenolol ............................78Pindolol .................................78Propranolol ............................78Timolol Maleate......................78Trans-U-50488H.....................72
ULMOα-Trityl-2-naphthalene
Propionic Acid ....................10α-Naphthyl Methyl Carbinol ....25β-Naphthyl Methyl Carbinol.....261,1’-Bi-2-Naphthol ..................261,1’-Binaphthol
Monomethylether.................281,1,2,-Triphenyl-1,2-
Ethanediol ..........................271,2,3,4-Tetrahydro-1-
Naphtol .............................251,3,5-Triphenylpent-4-yn-1-one 181-Cyclohexyl-1-
phenylacetic Acid................141-Cyclopentyl-1-
phenylacetic Acid................141-(4-Benzyloxy) Phenyl
Ethanol...............................301-(4-Hydroxyphenyl) Ethanol ....291-(4-Methoxyphenyl)-2-butanol..291-(4-Methoxyphenyl)-
2-propanol .........................291-[(4-Phenyl) Phenyl] Ethanol ....301-(m-Chlorophenyl) Ethanol ......311-(m-Methylphenyl) Ethanol ......301-(m-Trifluoromethylphenyl)
Ethanol...............................301-Naphthyl-2-Butanol...............261-(o-Chlorophenyl) Ethanol .......311-(o-Methoxyphenyl) Ethanol ....291-(o-Methylphenyl) Ethanol .......301-(p-Bromophenyl) Ethanol .......30
1-(p-Chlorophenyl) Ethanol.......311-(p-Fluorophenyl) Ethanol........301-(p-Methylphenyl) Ethanol .......301-Phenylpentanol ....................271-Phenyl-2-propanol ................292-(2-Chloro-4-methylphenoxy)
Propionic Acid ....................142-(4-Hydroxy-Phenoxy)
Propionic Acid ....................102-Methoxyphenyl Phenyl
Carbinol.............................282-Naphthyl-2-Butanol...............262-Thiopheneethanol.................292,3-Dibenzoyl-Tartaric Acid .....153-Thiopheneethanol.................299-Anthryl Trifluoromethyl
Carbinol.............................259-Anthrylethanol .....................26Acenaphthenol .......................25Althiazide ..............................71Bendroflumethiazide ...............67Calcium Channel Blocker.........12Cyclothiazide.........................61Cyclopentyl Benzoyl-diamide ...24Ditoluoyltartaric Acid ..............14Etodolac ..................................8Flobufen Metabolites ...............68Flobufen ................................68Indapamide ...........................67Ketoprofen as 1-
naphthylamide ......................8Methyl 3-Phenyl-3azido-
2-hydroxypropanoate (Erythro-diastereomer) ..........29
Naproxen................................9Phenyl Cyclohexyl Carbinol .....28Phenyl Ethyl Carbinol ..............27Phenyl Isopropyl Carbinol........28Phenyl Methyl Carbinol ...........27Phenyl Phenylethyl Carbinol .....28Phenyl Propyl Carbinol ............27Phenyl Tribromomethyl
Carbinol.............................27Phenylbutyric Acid ..................11Phenylsuccinic Acid ................13Prilocaine ..............................70Temazepam ...........................64Tert Butyl Phenyl Carbinol........25Tetrahydropyrimidine
Carboxylic Acid ..................11Thalidomide ...........................67Trans Phenyl Cyclohexanol
(Analytical vs. Preparative Run)..................28
Trichlormethiazide ..................70Trolox....................................12Trolox-methylether ...................14Vapol ....................................46Warfarin ...............................68
Whelk-O 1 and 2α-Methoxyphenyl Acetic Acid......................................131’-Acetoxychavicol Acetate ......191,1’-Binaphthyl-2,2’-
Diylhydrogen Phosphate.......122-(3-Chlorophenoxy)
Propionic Acid ....................142-cis-4-trans-Abscisic Acid .......752-Methyl-1-Indanone................162-Methyl-1-Tetralone................182-Phenylcyclopropane
Carboxylate........................122-trans-4-trans-Abscisic Acid.....753-Methyl-1-Indanone................174-Chloromandelic Acid............134-(Trifluoromethyl)-
Mandelic Acid ....................15Abscisic Acid .........................76Abscisic Acid Methyl Ester .......75Alfuzosin ...............................72Amlodipine ............................46Anisoin..................................32Bendroflumethiazide ...............61Benzoin .................................32BOC-Ala................................20Bromacil ................................56Buckminsterfullerene-Enone
[2+2] Photoadducts .............19Bupivacaine ...........................62Calanolide A .........................75Carprofen..............................11CBZ nornicotine .....................20CBZ-Phe ................................20CBZ-Val .................................20Chlorflurecol Methyl ................58Chlormezanone......................72Chrysanthemic Acid-
Ethyl Ester...........................57Cicloprofen...........................8,9Combretastatin D-1 .................75Coumachlor ...........................69Cromakalim ...........................70Crotoxyphos ..........................58Cyclandelate..........................62Cyclophosphamide .................37Devrinol, Napropamide...........58Dexmedetomidine ...................68Diclofop Methyl ......................58Dihydrotetrabenazine..............72Dinocap ................................60Doxazosin .............................72DPHB ....................................17EEDQ....................................20Ethotoin .................................71Ethyl-2-(p-Hydroxyphenoxy)
Propionate..........................19Fenvalerate ............................60Fenoprofen ..............................8
Index of Application by Column Type continued on page 90
90 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
INDEX OF APPLICATION BY COLUMN TYPE continued from page 89
Flavanone..............................75Flurbiprofen .............................9Fluridil ...................................72Hanessian’s Lignan .................63Hydrobenzoin ........................32Hydratropic Acid....................11Ibuprofen.................................9Ibuprofenol ............................25Idazoxan ...............................73Ifenprodil ...............................69Indapamide ...........................62Indoprofen .............................10Ipsdienol................................32Isoxsuprine.............................70Isradipine (normal phase) ........63Isradipine (reversed phase) ......63Ketamine ...............................69Ketoconazole .........................69Ketoprofen...............................8Ketorolac ...............................13Kynurenine.............................80Leptophos, Phosvel..................57Lorazepam.............................71Lorglumide .............................73Loxoprofen...............................9Mandelic Acid .......................12m-Cl-Styrene Oxide .................24McN 5652 ............................62Mecoprop..............................57Mecoprop Methyl ...................56Mephenytoin..........................61Mesogens ..............................47Metalaxyl ..............................57Methyl Mandelate...................16Metolachlor............................57Metolazone............................71Modafinil...............................73Mosapride .............................73Nadifloxacin..........................73Nadolol.................................78Naproxen (normal phase).....9,10Naproxen (reversed phase) .......9Naproxen (semi prep) ...............8Naproxen Diisopropyl Amide ....9Naproxen Dimethyl Amide ......10Naproxen Methyl Amide .........10Naproxen Methyl Ester............10Nicardipine ...........................63Nimodipine............................46Nirvanol ................................61Ofloxacin ..............................70Omite....................................57Oxazepam ............................61p-Chloro-Warfarin...................62Pazufloxacin ..........................72Permethrin .............................56Phenylethylene Glycol .............31Phototriggers ..........................47Pirprofen..................................8PPO Inhibitors ..............56,58,59Proglumide ............................64Propafenone ..........................28
Propiconazole, Tilt ..................58Quinazolone Derivatives ....68,69Ranolazine.............................31Rebamipide ...........................10Resmethrin .............................57SC 41930 .............................63Sethoxydim ............................57Silvex Methyl .........................59Stilbene Oxide .......................24Styrene Oxide ........................24Sulfinpyrazone .......................34Sulfone Atropisomer................41Sulfoxide Atropisomer .............41Sulindac ................................73Suprofen................................14Taxifolin ................................76Temazepam ...........................70Terfenadine............................28Tert-butyl-2(benzamido)
cyclopentyl carbamate ........19Tetrabenazine ........................72Tetrahydrobenzopyrene-7-ol.....26Tetrahydropalmatine ...............76Tetramethrin ...........................56Tetramisole ............................59Thalidomide ...........................61Tiaprofenic Acid.......................8Tolperisone ............................62Troger’s Base .........................15Troglitazone...........................64Trolox....................................12Tropicamide...........................63U-100057 .............................63U-94863 ..........................63,63Vanilmandelic Acid.................14Warfarin (normal phase) .........70Warfarin (reversed phase) .......70Zopiclone ..............................71
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Compound Structure/Name
This compound � may or � may notbe used in an application booklet.
Chiral ScreeningData SheetContact Information:
Primary Contact____________________________________
Other Contact _____________________________________
Company Address___________________________________
_____________________________________________
City___________________________________________
State _____________ Zip Code _____________________
Country ________________________________________
Phone _________________________________________
Fax___________________________________________
e-mail _________________________________________
_____________________________________________
Separation Requirements:Analytical �
Preparative �
Quantity ____________ � mg � gr � kg
Physical, Chemical, and Chromatographic Data:MSDS Available � Yes � No If yes, include a copy with your sample.
Hazardous Material � Yes � No � Unknown
Special Handling Requirements � Yes � No � Unknown
Appearance:� Powder � Crystal � Oil � Other
Color __________________ pKa __________________ UV (max) __________________ UV (min) __________________
Chemical Purity __________________
Do you want your sample returned?� Yes � No
Please Note: All samples are destroyed after the screeningprocess is complete.
REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 91
�
Stability/Exposure:Light � Stable � Decomposes � Unknown
Moisture � Stable � Decomposes � Unknown
Temp<40˚C � Stable � Decomposes � Unknown
ACIDS:
Acetic Acid (<1%) � Stable � Decomposes � Unknown
Trifluoroacetic Acid (<1%) � Stable � Decomposes � Unknown
BASES:
Triethylamine (<1%) � Stable � Decomposes � Unknown
Diethylamine (<1%) � Stable � Decomposes � Unknown
Storage Conditions:____________________________________________________________________________________________
_____________________________________________________________________________________________________________
SolubilityWater � Soluble � Slightly � Decomposes � Unknown
Methanol � Soluble � Slightly � Decomposes � Unknown
Ethanol � Soluble � Slightly � Decomposes � Unknown
2-Propanol � Soluble � Slightly � Decomposes � Unknown
Hexane � Soluble � Slightly � Decomposes � Unknown
Ethyl Acetate � Soluble � Slightly � Decomposes � Unknown
CH2Cl2 � Soluble � Slightly � Decomposes � Unknown
Acetonitrile � Soluble � Slightly � Decomposes � Unknown
Other ________________________________________________________________________________________________________
_____________________________________________________________________________________________________________
Chromatographic Analysis:
Column ______________________________________________
Column Manufacturer __________________________________
Mobile Phase _________________________________________
Flow Rate ______________ Wavelength __________________
Please include a copy of the chromatogram.
Chiral Screening Data Sheet
Instructions:Please send the completed form along with your sample. We would like to have at least 25 mg of sample. If youare unable to send us 25 mg, you must include sufficientsolubility information. If the compound you are sending isnot commercially available, please inquire if you need aconfidentiality agreement signed before you send us yoursample.
92 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/
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3/2007