Proline benzyl ester hydrochloride → 1-[(R)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

HRID 636993Notes

Reaction equation

HRID 636993 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([OH:9])=[O:8])=[O:4].Cl.[CH2:17]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:25]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:7](=[O:9])[C@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:31])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1.[CH2:17]([O:24][C:25]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:7](=[O:8])[C@@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:31])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2733413Proline benzyl ester hydrochlorideHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

Product 2

HCID 542807691-[(S)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl esterYield 15%HCID 542807701-[(R)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl esterYield 31%

Procedure

Reaction of 1.0 g of (R)-methoxycarbonylamino-phenyl-acetic acid and 1.16 g of (L)-proline benzyl ester hydrochloride according to the procedure described in example 91b gave 0.59 g (31%) of the title compound as a white solid and 0.28 g (15%) of 1-[(S)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester (+)-APCI-MS: 397 (MH+).

Sources & evidence

ORD record
ord-8f1fa657399b4eae8bd46494ec3502ab
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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