(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (R)-7-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-5-fluoro-1H-indole-2-carboxylic acid ethyl ester

HRID 853103Notes

Reaction equation

HRID 853103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[Br:16])=[O:5])[CH3:2].[C:17]([O:21][C:22]([N:24]1[CH2:28][C@H:27]([CH3:29])OS1(=O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C@H:27]([CH3:29])[CH2:28][NH:24][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[Br:16])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 21014457Ethyl 7-bromo-5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 69417576(R)-7-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-5-fluoro-1H-indole-2-carboxylic acid ethyl ester

Procedure

The title compound, ISP-MS: m/e=(M+H+), was prepared in accordance with the general method of example 12b) from 7-bromo-5-fluoro-1H-indole-2-carboxylic acid ethyl ester (10.0 g, 0.035mol) and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 10 g, 0.042 mol). The product was isolated as a viscous yellow oil, (10.1 g, 65%); ISP MS: 445.3 (M+H)+

Sources & evidence

ORD record
ord-df0f33cd1e1c400c96dae22e052eb5a8
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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