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

HRID 1697486Notes

Reaction equation

HRID 1697486 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].[SH:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][OH:35]>>[C:6]([O:10][C:11]([N:13]1[CH2:17][C@H:16]([S:31][C:32]2[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=2[CH2:34][OH:35])[CH2:15][C@H:14]1[C:23](=[O:30])[NH:24][C:25]1([C:28]#[N:29])[CH2:26][CH2:27]1)=[O:12])([CH3:8])([CH3:9])[CH3:7]

Participants

4

Reactant 3

HCID 85257MethanesulfonateHCID 1382782-MercaptobenzenemethanolHCID 59543742(2S,4S)-2-(1-cyano-cyclopropylcarbamoyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 67278389(2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(2-hydroxymethyl-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester

Procedure

The reaction of the mesylate from experiment A2 with 2-mercaptobenzyl alcohol yielded (2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(2-hydroxymethyl-phenylsulfanyl)-pyrrolidine-1-carboxylic acid t-butyl ester as a colorless oil. MS: 416.5 [M−H]−.

Sources & evidence

ORD record
ord-6d72ce3fb11e4a56a87ea21c36c63f07
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…