methyl L-prolinate hydrochloride → 1-[(R)-Ethoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid methyl ester

HRID 1279091Notes

Reaction equation

HRID 1279091 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=O)=[O:5])[CH3:2].Cl.[CH3:18][O:19][C:20](=[O:26])[C@@H:21]1[CH2:25][CH2:24][CH2:23][NH:22]1>>[CH3:18][O:19][C:20]([C@@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:8](=[O:10])[C@H:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:26]

Participants

3

Reactant 2

HCID 2733200methyl L-prolinate hydrochlorideHCID 16116512(R)-ethoxycarbonylamino-phenyl-acetic acid

Product 1

HCID 539394991-[(R)-Ethoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid methyl esterYield 57%

Procedure

Reaction of 2.0 g of (R)-ethoxycarbonylamino-phenyl-acetic acid and 1.50 g of (L)-proline methyl ester hydrochloride according to the procedure described for example 91b gave 1.70 g (57%) of the title compound as a colorless oil. (+)-APCI-MS: 335 (MH+).

Sources & evidence

ORD record
ord-eec2db3804ad4001bf5ee347df469f60
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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