Ethyl 4-chloro-1H-indole-2-carboxylate → (r)-1-(2-Tert-butoxycarbonylamino-1-methyl-ethyl)-4-chloro-1h-indole-2-carboxylic acid ethyl ester

HRID 853058Notes

Reaction equation

HRID 853058 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][CH:9]=2)=[O:5])[CH3:2].[C:16]([O:20][C:21]([N:23]1[CH2:27][C@H:26]([CH3:28])OS1(=O)=O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C@H:26]([CH3:28])[CH2:27][NH:23][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[C:8]2[C:13]([CH:14]=1)=[C:12]([Cl:15])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 11075028Ethyl 4-chloro-1H-indole-2-carboxylateHCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Product 1

HCID 69414316(r)-1-(2-Tert-butoxycarbonylamino-1-methyl-ethyl)-4-chloro-1h-indole-2-carboxylic acid ethyl ester

Procedure

The title compound, m.p.: 115–119° C., ISP-MS: m/e=381.3 (M+H+) and αD20=−8.0, was prepared in accordance with the general method of example 12b) from 4-chloro-1H-indole-2-carboxylic acid ethyl ester and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-68b3eba7136b49e7b692ba1ea0d0c83c
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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