4-Bromo-2-(trifluoromethyl)benzenethiol → (1R,2R,4S)-4-(4-Bromo-2-trifluoromethyl-phenylsulfanyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid ethyl ester

HRID 1367513Notes

Reaction equation

HRID 1367513 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9](OS(C)(=O)=O)[CH2:8][C@H:7]1[C:16]([N:18]1[CH2:21][C:20]([F:23])([F:22])[CH2:19]1)=[O:17])=[O:5])[CH3:2].[Br:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=1>>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([S:31][C:28]2[CH:29]=[CH:30][C:25]([Br:24])=[CH:26][C:27]=2[C:32]([F:35])([F:33])[F:34])[CH2:8][C@H:7]1[C:16]([N:18]1[CH2:19][C:20]([F:22])([F:23])[CH2:21]1)=[O:17])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 509979974-Bromo-2-(trifluoromethyl)benzenethiol2×HCID 86649025(1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 86649024(1R,2R,4S)-4-(4-Bromo-2-trifluoromethyl-phenylsulfanyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to Example 68/69, step 8, using (1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester and 4-Bromo-2-trifluoromethyl-benzenethiol (Example 58, intermediate 1). Light yellow oil. MS (EI): 518.0 (M+H)+.

Sources & evidence

ORD record
ord-54a877a9650446728ecf62b883e1b60c
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

Loading…