electronic supplementary information · 1 electronic supplementary information efficient asymmetric...
TRANSCRIPT
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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.
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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.
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LCMS of ((S)-4-benzyl-3-tert-butyl 1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide 1
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1H NMR spectrum (400 MHz, acetone-d6) of compound 4
1H NMR spectrum (400 MHz, MeOH-d4) of compound 4
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C NMR spectrum (100 MHz, MeOH-d4) of compound 4
APT NMR spectrum (100 MHz, MeOH-d4) of compound 4
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LCMS of compound 4
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 2ʹ(R = H)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6a
13C NMR spectrum (100 MHz, DMSO-d6) of compound 6a
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APT NMR spectrum (100 MHz, DMSO-d6) of compound 6a
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LCMS of compound 6a
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Chiral HPLC of 6a (L-isomer)
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Chiral HPLC of 6a (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6b
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6b
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6b
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LCMS of compound 6b
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Chiral HPLC of 6b (L-isomer)
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Chiral HPLC of 6b (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6c
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6c
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APT NMR spectrum (100 MHz, DMSO-d6) of compound 6c
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LCMS of compound 6c
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Chiral HPLC of 6c (L-isomer)
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Chiral HPLC of 6c (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6d
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6d
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6d
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LCMS spectrum of compound 6d
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Chiral HPLC of 6d (L-isomer)
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Chiral HPLC of 6d (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6e
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6e
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APT NMR spectrum (100 MHz, DMSO-d6) of compound 6e
LCMS spectrum of compound 6e
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6f
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6f
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APT NMR spectrum (100 MHz, DMSO-d6) of compound 6f
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LCMS spectrum of compound 6f
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6g
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13C NMR spectrum (100 MHz, DMSO-d6) of compound 6g
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6g
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LCMS spectrum of compound 6g
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6h
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6h
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APT NMR spectrum (100 MHz, DMSO-d6) of compound 6h
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LCMS spectrum of compound 6h
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Chiral HPLC of 6h (L-isomer)
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Chiral HPLC of 6h (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6i
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6i
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6i
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LCMS spectrum of compound 6i
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Chiral HPLC of 6i (L-isomer)
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Chiral HPLC of 6i (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6j
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6j
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6j
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LCMS spectrum of compound 6j
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Chiral HPLC of 6j (L-isomer)
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Chiral HPLC of 6j (D-isomer)
1H NMR spectrum (400 MHz, DMSO-d6) of compound 6k
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13C NMR spectrum (100MHz, DMSO-d6) of compound 6k
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6k
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LCMS spectrum of compound 6k
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6l
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13C NMR spectrum (100 MHz, DMSO-d6) of compound 6l
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6l
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LCMS spectrum of compound 6l
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Chiral HPLC of 6l (L-isomer)
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Chiral HPLC of 6l (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6m
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6m
APT
NMR spectrum (100 MHz, DMSO-d6) of compound 6m
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LCMS spectrum of compound 6m
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Chiral HPLC of 6m (L-isomer)
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Chiral HPLC of 6m (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6n
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C NMR spectrum (100 MHz, DMSO-d6) of compound 6n
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APT NMR spectrum (100 MHz, DMSO-d6) of compound 6n
LCMS spectrum of compound 6n
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6o
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13C NMR spectrum (100 MHz, DMSO-d6) of compound 6o
APT NMR spectrum (100MHz, DMSO-d6) of compound 6o
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LCMS spectrum of compound 6o
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Chiral HPLC of 6o (L-isomer)
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Chiral HPLC of 6o (D-isomer)
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1H NMR spectrum (400 MHz, DMSO-d6) of compound 6p
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C NMR spectrum (100MHz, DMSO-d6) of compound 6p
APT NMR spectrum (100 MHz, DMSO-d6) of compound 6p
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LCMS spectrum of compound 6p
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1H NMR (400 MHz, CDCl3) of compound 8
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13C NMR (100 MHz, CDCl3) of compound 8
APT (100 MHz, CDCl3) of compound 8
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1H NMR (400 MHz, CDCl3) of sulfamidate 9
1H NMR (400MHz, DMSO-d6) of sulfamidate 9
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LCMS of sulfamidate 9
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C NMR (100 MHz, CDCl3) of sulfamidate 9
APT (100 MHz, CDCl3) of sulfamidate 9
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1H NMR (400 MHz, DMSO-d6) of compound 10c
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13C NMR (100 MHz, DMSO-d6) of compound 10c
LCMS of compound 10c
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1H NMR (400 MHz, DMSO-d6) of compound 10d
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LCMS of compound 10d
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C NMR (100 MHz, DMSO-d6) of compound 10d
APT (100 MHz, DMSO-d6) of compound 10d
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Chiral HPLC of L-Isomer of compound 10d
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Chiral HPLC of D-Isomer of compound 10d
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1H NMR (400 MHz, DMSO-d6) of compound 10f
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LCMS of compound 10f
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C NMR (100 MHz, DMSO-d6) of compound 10f
APT (100 MHz, DMSO-d6) of compound 10f
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1H NMR (400 MHz, DMSO-d6) of compound 10g
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LCMS of compound 10g
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C NMR (100 MHz, DMSO- d6 + TFA) of compound 10g
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1H NMR (400 MHz, DMSO-d6) of compound 10j
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LCMS of compound 10j
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C NMR (100 MHz, DMSO-d6) of compound 10j
APT (100 MHz, DMSO-d6) of compound 10j
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Chiral HPLC of L-isomer of 10j
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Chiral HPLC of D-Isomer of 10j
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1H NMR (400 MHz, DMSO-d6) of compound 10m
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LCMS of compound 10m
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C NMR (100 MHz, DMSO-d6) of compound 10m
APT (100 MHz, DMSO-d6) of compound 10m
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1H NMR (400 MHz, DMSO-d6) of compound 10o
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LCMS of compound 10o
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C NMR (100 MHz, DMSO-d6) of compound 10o
APT (100 MHz, DMSO-d6) of compound 10o
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1H NMR (400 MHz, MeOD) of compound 10q
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LCMS of compound 10q
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C NMR (100 MHz, MeOD + 3 drop CDCl3) of compound 10q
APT (100 MHz, MeOD + 3 drop CDCl3) of compound 10q
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Chiral HPLC of L-isomer of 10q
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Chiral HPLC of D-isomer of 10q