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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


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


Chiralyser664-N,N-dimethyl alcohol-OBH, %10,1mL, 254nm


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)


Chiralyser18-04-2017(%1 0 IPA-HEX. 1 mL,254 nm,OB-H)


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


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)


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


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


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)


2.91

4.49

4.48

0.48

0.47

0.95

0.44

0.46

0.64

1.00

-100102030405060708090100110120130140150160170180190200f1 (ppm)

13C OBSERVE


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)


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


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)



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)


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


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)


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


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


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)



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)


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)


10.0

5

2.42

4.61

0.79

0.80

2.23

2.24

1.00

102030405060708090100110120130140150160170180190200210220f1 (ppm)

170175180185190195200205210f1 (ppm)


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)



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


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)


9.43

6.37

2.02

0.92

0.87

2.14

1.00

10.610.710.810.911.011.1f1 (ppm)


0102030405060708090100110120130140150160170180190200f1 (ppm)



0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)


4.04

1.18

0.42

0.60

1.03

1.00

-100102030405060708090100110120130140150160170180190200210220230f1 (ppm)



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)



102030405060708090100110120130140150160170180190200f1 (ppm)



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