1,2,3-Oxathiazolidine-3-carboxylic acid, 4-methyl-, 1,1-dimethylethyl ester, 2,2-dioxide, (4S)- → (S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

HRID 2249587Notes

Reaction equation

HRID 2249587 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][NH:15]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:18]([O:22][C:23]([N:25]1[C@@H:29]([CH3:30])[CH2:28]OS1(=O)=O)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23](=[O:24])[NH:25][C@@H:29]([CH3:28])[CH2:30][N:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH:17]=2)[CH:13]=[CH:14]1)([CH3:21])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 109882941,2,3-Oxathiazolidine-3-carboxylic acid, 4-methyl-, 1,1-dimethylethyl ester, 2,2-dioxide, (4S)-HCID 152927466-(4-methoxyphenyl)-1H-indole

Product 1

HCID 67031552(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

Procedure

This compound was synthesized from 6-(4-methoxy-phenyl)-indole (synthesized from 6-bromo-indole according to Carrera, G. M. et al. Synlett 1994, 1, 93-94) and (S)-4-methyl-2,2-dioxo-[1,2,3] oxathiazolidine-3-carboxylic acid tert-butyl ester as described in example 4, step A].

Sources & evidence

ORD record
ord-9fe59b166a7a4d138bc39e61bfba10e1
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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