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

HRID 2304331Notes

Reaction equation

HRID 2304331 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:29])[C@H:17]([NH:24][C:25]([O:27][CH3:28])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:10])C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[CH3:28][O:27][C:25]([NH:24][C@H:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:29])=[O:26]

Participants

5

Reactant 1

HCID 542807701-[(R)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

Product 1

HCID 229584921-[(R)-Methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acidYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of 1-[(R)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester were dissolved in a mixture of 15 mL of methanol and 15 ML of tetrahydrofuran and hydrogenated for 3 h at room temperature using 0.4 g palladium on charcoal (10%) as catalyst. Filtration followed by concentration in vacuo affords 0.45 g (100%) of the title compound as a white solid. (+)-APCI-MS: 307 (MH+).

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-8ec8efc1c7f6454c826371459a1ed67b
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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