Lithium Hydroxide → 1-[(R)-Isopropoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid

HRID 1008560Notes

Reaction equation

HRID 1008560 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:25])[C@H:11]([NH:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[Li+].[OH-].OS([O-])(=O)=O.[K+].C(OCC)(=O)C>CO.O>[CH:22]([O:21][C:19]([NH:18][C@H:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])=[O:25])=[O:20])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 545024061-[(R)-Isopropoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid methyl ester

Product 1

HCID 229584901-[(R)-Isopropoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acidYield 83.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-[(R)-isopropoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid methyl ester (0.95 g) and 0.13 g of LiOH in 20 mL of methanol and 5 mL of water was stirred for 16 h at ambient temperature. KHSO4 was added, the volatiles were pumped off followed by addition of water, extraction with ethyl acetate and concentration of the organic layer to give 0.76 g (83%) of the title compound as a white solid. (+)-APCI-MS: 335 (MH+).

Sources & evidence

ORD record
ord-3fe1a5c2c97240f0aee932aa7a6c6c8a
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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