Thiophenol → HCID 66918764, compound

HRID 1367463Notes

Reaction equation

HRID 1367463 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9](OS(C)(=O)=O)[CH2:8][C@H:7]1[C:16](=[O:23])[NH:17][C:18]1([C:21]#[N:22])[CH2:20][CH2:19]1)=[O:5])[CH3:2].[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([S:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][C@H:7]1[C:16](=[O:23])[NH:17][C:18]1([C:21]#[N:22])[CH2:19][CH2:20]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 7969ThiophenolHCID 86649016HCID 86649016, compound

Product 1

HCID 66918764HCID 66918764, compound

Procedure

The reaction of the mixture of (1R,2R,4R) and (1R,2R,4S)-2-(1-cyano-cyclopropylcarbamoyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester from step 3 with thiophenol performed in analogy to example 1, step 5, yielded a crude material which was purified on silica using n-heptane/EtOAc (3:2) to give in the first fraction the desired (1R,2R,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-phenylsulfanyl-cyclopentanecarboxylic acid ethyl ester as a colorless oil. MS: 359.2 (M+H)+.

Workup

  1. customyielded a crude material which
  2. customwas purified on silica

Sources & evidence

ORD record
ord-9553e535394a4ee5a0814596846f75d1
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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