Methanesulfonate → (2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(4-imidazol-1-yl-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester

HRID 1697488Notes

Reaction equation

HRID 1697488 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].[N:31]1([C:36]2[CH:41]=[CH:40][C:39]([SH:42])=[CH:38][CH:37]=2)[CH:35]=[CH:34][N:33]=[CH:32]1>>[C:6]([O:10][C:11]([N:13]1[CH2:17][C@H:16]([S:42][C:39]2[CH:38]=[CH:37][C:36]([N:31]3[CH:35]=[CH:34][N:33]=[CH:32]3)=[CH:41][CH:40]=2)[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]

Participants

4

Reactant 3

HCID 85257MethanesulfonateHCID 214816514-(1H-Imidazol-1-yl)benzene-1-thiolHCID 59543742(2S,4S)-2-(1-cyano-cyclopropylcarbamoyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 67278336(2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(4-imidazol-1-yl-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester

Procedure

The reaction of the mesylate from experiment A2 with 4-imidazol-1-yl-benzenethiol (prepared according to patent application FR 2267101, 1975) yielded (2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(4-imidazol-1-yl-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester as a colorless foam. MS: 454.2 [M+H]+.

Sources & evidence

ORD record
ord-550e248eb0454f3fb03b5dc3de0526ad
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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