2-Chloro-4-fluorothiophenol → (1R,2R,4S)-4-(2-Chloro-4-fluoro-phenylsulfanyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid ethyl ester

HRID 1367518Notes

Reaction equation

HRID 1367518 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].[F:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[C:27]([Cl:32])[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]([F:24])=[CH:26][C:27]=2[Cl:32])[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 5194462-Chloro-4-fluorothiophenolHCID 86649025(1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 66918952(1R,2R,4S)-4-(2-Chloro-4-fluoro-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 (Example 117, step 3) and 4-fluoro-2-chloro-benzenethiol. Light yellow solid. MS (EI): 422.7 (M+H)+.

Sources & evidence

ORD record
ord-798b9b3987384e4d962b84857a1f50cc
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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