electronic supplementary information · 1 electronic supplementary information efficient asymmetric...
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Electronic Supplementary Information
Efficient asymmetric synthesis of N-protected--
aryloxyamino acids via regioselective ring
opening of serine sulfamidate carboxylic acid
Rajesh Malhotra,a Tushar K. Dey,
a,b Swarup Dutta,
b Sourav Basu*
b and Saumen Hajra*
c
a Guru Jambheshwar University of Science and Technology, Hisar, Haryana 125001, India.
b TCG Life Sciences Ltd, Saltlake, Kolkata 700091, India, and Department of Chemistry,
c Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India;
[email protected]; [email protected]
Contents
NMR Spectra, LC-MS and HPLC Chromatogram
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014
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NMR Spectra, LC-MS and Chromatogram
1H NMR spectrum (400 MHz, CDCl3) of (S)-4-benzyl-3-tert-butyl 1,2,3-oxathiazolidine-3,4-
dicarboxylate 2,2-dioxide 1.
13
C NMR spectrum (100 MHz, CDCl3) of (S)-4-benzyl-3-tert-butyl 1,2,3-oxathiazolidine-
3,4-dicarboxylate 2,2-dioxide 1.
3
APT NMR spectrum (100MHz, CDCl3) of (S)-4-benzyl-3-tert-butyl 1,2,3-oxathiazolidine-
3,4-dicarboxylate 2,2-dioxide 1.
IR of ((S)-4-benzyl-3-tert-butyl 1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide 1.
4
LCMS of ((S)-4-benzyl-3-tert-butyl 1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide 1
5
1H NMR spectrum (400 MHz, acetone-d6) of compound 4
1H NMR spectrum (400 MHz, MeOH-d4) of compound 4
6
13
C NMR spectrum (100 MHz, MeOH-d4) of compound 4
APT NMR spectrum (100 MHz, MeOH-d4) of compound 4
7
LCMS of compound 4
8
1H NMR spectrum (400 MHz, DMSO-d6) of compound 2ʹ(R = H)
9
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6a
13C NMR spectrum (100 MHz, DMSO-d6) of compound 6a
10
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6a
11
LCMS of compound 6a
12
Chiral HPLC of 6a (L-isomer)
13
Chiral HPLC of 6a (D-isomer)
14
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6b
15
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6b
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6b
16
LCMS of compound 6b
17
Chiral HPLC of 6b (L-isomer)
18
Chiral HPLC of 6b (D-isomer)
19
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6c
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6c
20
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6c
21
LCMS of compound 6c
22
Chiral HPLC of 6c (L-isomer)
23
Chiral HPLC of 6c (D-isomer)
24
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6d
25
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6d
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6d
26
LCMS spectrum of compound 6d
27
Chiral HPLC of 6d (L-isomer)
28
Chiral HPLC of 6d (D-isomer)
29
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6e
30
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6e
31
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6e
LCMS spectrum of compound 6e
32
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6f
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6f
33
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6f
34
LCMS spectrum of compound 6f
35
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6g
36
13C NMR spectrum (100 MHz, DMSO-d6) of compound 6g
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6g
37
LCMS spectrum of compound 6g
38
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6h
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6h
39
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6h
40
LCMS spectrum of compound 6h
41
Chiral HPLC of 6h (L-isomer)
42
Chiral HPLC of 6h (D-isomer)
43
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6i
44
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6i
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6i
45
LCMS spectrum of compound 6i
46
Chiral HPLC of 6i (L-isomer)
47
Chiral HPLC of 6i (D-isomer)
48
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6j
49
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6j
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6j
50
LCMS spectrum of compound 6j
51
52
Chiral HPLC of 6j (L-isomer)
53
Chiral HPLC of 6j (D-isomer)
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6k
54
13C NMR spectrum (100MHz, DMSO-d6) of compound 6k
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6k
55
LCMS spectrum of compound 6k
56
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6l
57
13C NMR spectrum (100 MHz, DMSO-d6) of compound 6l
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6l
58
LCMS spectrum of compound 6l
59
Chiral HPLC of 6l (L-isomer)
60
Chiral HPLC of 6l (D-isomer)
61
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6m
62
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6m
APT
NMR spectrum (100 MHz, DMSO-d6) of compound 6m
63
LCMS spectrum of compound 6m
64
Chiral HPLC of 6m (L-isomer)
65
Chiral HPLC of 6m (D-isomer)
66
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6n
67
13
C NMR spectrum (100 MHz, DMSO-d6) of compound 6n
68
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6n
LCMS spectrum of compound 6n
69
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6o
70
13C NMR spectrum (100 MHz, DMSO-d6) of compound 6o
APT NMR spectrum (100MHz, DMSO-d6) of compound 6o
71
LCMS spectrum of compound 6o
72
Chiral HPLC of 6o (L-isomer)
73
Chiral HPLC of 6o (D-isomer)
74
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6p
75
13
C NMR spectrum (100MHz, DMSO-d6) of compound 6p
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6p
76
LCMS spectrum of compound 6p
77
1H NMR (400 MHz, CDCl3) of compound 8
78
13C NMR (100 MHz, CDCl3) of compound 8
APT (100 MHz, CDCl3) of compound 8
79
1H NMR (400 MHz, CDCl3) of sulfamidate 9
1H NMR (400MHz, DMSO-d6) of sulfamidate 9
80
LCMS of sulfamidate 9
81
13
C NMR (100 MHz, CDCl3) of sulfamidate 9
APT (100 MHz, CDCl3) of sulfamidate 9
82
1H NMR (400 MHz, DMSO-d6) of compound 10c
83
13C NMR (100 MHz, DMSO-d6) of compound 10c
LCMS of compound 10c
84
1H NMR (400 MHz, DMSO-d6) of compound 10d
85
LCMS of compound 10d
86
13
C NMR (100 MHz, DMSO-d6) of compound 10d
APT (100 MHz, DMSO-d6) of compound 10d
87
Chiral HPLC of L-Isomer of compound 10d
88
Chiral HPLC of D-Isomer of compound 10d
89
1H NMR (400 MHz, DMSO-d6) of compound 10f
90
LCMS of compound 10f
91
13
C NMR (100 MHz, DMSO-d6) of compound 10f
APT (100 MHz, DMSO-d6) of compound 10f
92
1H NMR (400 MHz, DMSO-d6) of compound 10g
93
LCMS of compound 10g
94
13
C NMR (100 MHz, DMSO- d6 + TFA) of compound 10g
95
1H NMR (400 MHz, DMSO-d6) of compound 10j
96
LCMS of compound 10j
97
13
C NMR (100 MHz, DMSO-d6) of compound 10j
APT (100 MHz, DMSO-d6) of compound 10j
98
Chiral HPLC of L-isomer of 10j
99
Chiral HPLC of D-Isomer of 10j
100
1H NMR (400 MHz, DMSO-d6) of compound 10m
101
LCMS of compound 10m
102
13
C NMR (100 MHz, DMSO-d6) of compound 10m
APT (100 MHz, DMSO-d6) of compound 10m
103
1H NMR (400 MHz, DMSO-d6) of compound 10o
104
LCMS of compound 10o
105
13
C NMR (100 MHz, DMSO-d6) of compound 10o
APT (100 MHz, DMSO-d6) of compound 10o
106
1H NMR (400 MHz, MeOD) of compound 10q
107
LCMS of compound 10q
108
13
C NMR (100 MHz, MeOD + 3 drop CDCl3) of compound 10q
APT (100 MHz, MeOD + 3 drop CDCl3) of compound 10q
109
Chiral HPLC of L-isomer of 10q
110
Chiral HPLC of D-isomer of 10q