SUPPORTING INFORMATION Reaction of (S)-homoserine lactone with Grignard reagents: Synthesis of amino-keto-alcohols and β-amino acid derivatives Özlem GÜNDOĞDU, Pınar TURHAN, Aytekin KÖSE, Ramazan ALTUNDAŞ, Yunus KARA* Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey 60 Minutes 0 2 4 6 8 10 12 14 16 18 20 mAU 0,0 0,1 0,2 0,3 0,4 0,5 U V D edector-254nm Ethyl-S ilyl-O B H,% 10,1m L,254nm R etention Tim e Area P ercent C hiralyser Ethyl-S ilyl-O B H,% 10,1m L,254nm Retention Tim e A reaPercent HPLC analysis of 8a'
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SUPPORTING INFORMATION
Reaction of (S)-homoserine lactone with Grignard reagents: Synthesis of amino-keto-alcohols and β-amino acid derivatives
Özlem GÜNDOĞDU, Pınar TURHAN, Aytekin KÖSE, Ramazan ALTUNDAŞ, Yunus KARA*
Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey
60
Minutes0 2 4 6 8 10 12 14 16 18 20
mA
U
0,0
0,1
0,2
0,3
0,4
0,5UV Dedector-254nmEthyl-Silyl-OBH, %10,1mL, 254nm
Retention TimeArea Percent
ChiralyserEthyl-Silyl-OBH, %10,1mL, 254nm
Retention TimeArea Percent
HPLC analysis of 8a'
60
Minutes0 5 10 15 20 25 30 35 40 45 50
mA
U
0,0
0,1
0,2
0,3
0,4
0,5UV Dedector-254nm664-N,N-dimethyl alcohol-OBH, %10,1mL, 254nm
Retention TimeArea Percent
Chiralyser664-N,N-dimethyl alcohol-OBH, %10,1mL, 254nm
Retention TimeArea Percent
HPLC analysis of 6k
15
Minutes0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
mA
U
0
2
4
6
8
10
12
14
3,8
100
,0
UV Dedector-254nm18-04-2017(%1 0 IPA-HEX. 1 mL,254 nm,OB-H)
Retention TimeArea Percent
Chiralyser18-04-2017(%1 0 IPA-HEX. 1 mL,254 nm,OB-H)
Retention TimeArea Percent
HPLC analysis of 6j’
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
pan-240415-1hnmrSTANDARD 1H OBSERVE
10.9
7
1.34
2.33
3.56
1.04
0.91
2.37
1.24
1.00
0102030405060708090100110120130140150160170180190200f1 (ppm)
pan-240415-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
ogu-011015-1hnmrSTANDARD 1H OBSERVE
3.01
4.43
4.42
0.71
0.60
1.05
1.50
0.52
0.44
0.61
1.00
0102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-011015-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
ake-290915-1hnmrSTANDARD 1H OBSERVE
7.77
2.55
1.97
2.91
2.75
1.24
0.98
1.74
1.06
1.00
102030405060708090100110120130140150160170180190200210f1 (ppm)
140150160170180190200210f1 (ppm)
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
bdr-070515-1hnmrSTANDARD 1H OBSERVE
3.89
6.07
4.79
0.73
0.58
1.69
1.32
0.50
0.47
1.51
1.00
0102030405060708090100110120130140150160170180190200f1 (ppm)
bdr-070515-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
ake-280915-2-1hnmrSTANDARD 1H OBSERVE
3.20
4.82
4.39
0.58
0.57
1.08
0.53
0.44
1.03
1.00
0102030405060708090100110120130140150160170180190200f1 (ppm)
ake-280915-2-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
pan-270415-1hnmrSTANDARD 1H OBSERVE
2.91
4.49
4.48
0.48
0.47
0.95
0.44
0.46
0.64
1.00
-100102030405060708090100110120130140150160170180190200f1 (ppm)
13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
ake-1400417-1hnmrSTANDARD 1H OBSERVE
7.27
11.3
0
10.1
9
1.42
1.12
2.53
1.10
0.94
0.97
1.00
-100102030405060708090100110120130140150160170180190200f1 (ppm)
ake-1400417-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
ogu-281215-1hnmrSTANDARD 1H OBSERVE 4.
79
0.61
2.99
1.09
0.53
0.58
0.49
1.08
1.00
102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-281215-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.20.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.0f1 (ppm)
ake-271213-1hnmrSTANDARD 1H OBSERVE
7.41
11.7
4
3.56
11.0
5
2.43
2.33
2.38
1.04
1.00
-20-100102030405060708090100110120130140150160170180190200210f1 (ppm)
13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
ake-251213-1hnmrSTANDARD 1H OBSERVE
7.85
11.6
3
7.16
12.1
4
1.15
1.61
1.12
2.63
1.10
1.00
0102030405060708090100110120130140150160170180190200210f1 (ppm)
13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
ogu-060116-2-1hnmrSTANDARD 1H OBSERVE
12.5
7
2.81
0.98
1.09
4.10
2.62
1.00
102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-060116-2-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
ogu-060116-5-1hnmrSTANDARD 1H OBSERVE 12
.71
2.30
3.08
0.93
0.98
2.27
1.07
1.00
102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-060116-5-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
ogu-130116-1-1hnmrSTANDARD 1H OBSERVE 6.
12
0.66
0.53
1.74
0.42
1.07
1.00
0102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-130116-1-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CD3OD)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.0f1 (ppm)
pan-040116-1hnmrSTANDARD 1H OBSERVE
10.0
5
2.42
4.61
0.79
0.80
2.23
2.24
1.00
102030405060708090100110120130140150160170180190200210220f1 (ppm)
170175180185190195200205210f1 (ppm)
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CD3OD)
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
ogu-130116-2-1hnmrSTANDARD 1H OBSERVE 8.
08
2.65
2.09
2.66
4.67
0.73
2.84
1.00
102030405060708090100110120130140150160170180190200210f1 (ppm)
ogu-130116-2-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CD3OD)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
STANDARD 1H OBSERVE 4.
60
1.46
1.08
0.46
0.50
1.31
1.00
102030405060708090100110120130140150160170180190200f1 (ppm)
pan-041115-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
ogu-110116-1hnmrSTANDARD 1H OBSERVE
9.43
6.37
2.02
0.92
0.87
2.14
1.00
10.610.710.810.911.011.1f1 (ppm)
ogu-110116-1hnmrSTANDARD 1H OBSERVE
0102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-110116-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
ogu-291215-1hnmrSTANDARD 1H OBSERVE
4.04
1.18
0.42
0.60
1.03
1.00
-100102030405060708090100110120130140150160170180190200210220230f1 (ppm)
ogu-291215-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
ogu-130116-1hnmrSTANDARD 1H OBSERVE 3.
40
0.42
0.41
0.29
0.72
1.00
102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-130116-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CD3OD)
102030405060708090100110120130140150160170180190200f1 (ppm)
ogu-140515-2-13cnmr13C OBSERVE
400 MHz 1H NMR and 100 MHz 13C NMR spectrum (CDCl3)
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