2,4-Dichlorobenzenethiol → (2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(2,4-dichloro-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester

HRID 1697489Notes

Reaction equation

HRID 1697489 reaction equation
S([O-])(=O)(=O)C.[C:6]([O:10][C:11]([N:13]1[CH2:17][C@@H:16](OS(C)(=O)=O)[CH2:15][C@H:14]1[C:23](=[O:30])[NH:24][C:25]1([C:28]#[N:29])[CH2:27][CH2:26]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[SH:39]>>[C:6]([O:10][C:11]([N:13]1[CH2:17][C@H:16]([S:39][C:33]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:32]=2[Cl:31])[CH2:15][C@H:14]1[C:23](=[O:30])[NH:24][C:25]1([C:28]#[N:29])[CH2:27][CH2:26]1)=[O:12])([CH3:8])([CH3:9])[CH3:7]

Participants

4

Reactant 3

HCID 707302,4-DichlorobenzenethiolHCID 85257MethanesulfonateHCID 59543742(2S,4S)-2-(1-cyano-cyclopropylcarbamoyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 67278396(2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(2,4-dichloro-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester

Procedure

The reaction of the mesylate from experiment A2 with 2,4-dichlorothiophenol yielded ((2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(2,4-dichloro-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester as a colorless oil. MS: 454.3 [M−H]−.

Sources & evidence

ORD record
ord-c48dd0312d064ac0a7a6903d90e250b7
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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