(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-4-chloro-7-fluoro-1H-indole-2-carboxylic acid ethyl ester

HRID 585831Notes

Reaction equation

HRID 585831 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([Cl:15])[CH:11]=[CH:10][C:9]=2[F: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)=[C:12]([Cl:15])[CH:11]=[CH:10][C:9]=2[F: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 694157714-chloro-7-fluoro-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 69414753(R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-4-chloro-7-fluoro-1H-indole-2-carboxylic acid ethyl ester

Procedure

The title compound, ISP-MS: m/e=399.4 (M+H+) and α D 20 = - 54.7 , was prepared in accordance with the general method of example 12b) from 4-chloro-7-fluoro-1H-indole-2-carboxylic acid ethyl ester and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester. e) (R)-9-Chloro-6-fluoro-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Sources & evidence

ORD record
ord-13fecf8bd04646e3913976d8072bed8c
Source dataset
uspto-grants-2005_08
Patent number
US06933387B2

Reaction notes

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