1-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidin-2-(S)-carboxylic acid benzyl ester → 1-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidine-2-(S)-carboxylic acid

HRID 2304320Notes

Reaction equation

HRID 2304320 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:35])[C@H:17]([NH:31][C:32](=[O:34])[CH3:33])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:32]([NH:31][C@H:17]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:35])(=[O:34])[CH3:33]

Participants

4

Reactant 1

HCID 697804591-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidin-2-(S)-carboxylic acid benzyl ester

Product 1

HCID 229584291-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidine-2-(S)-carboxylic acidYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidine-2-(S)-carboxylic acid benzyl ester (0.50 g) were dissolved in 30 mL of methanol and hydrogenated for 4 h at room temperature using 0.3 g palladium on charcoal (10%) as catalyst. Filtration followed by concentration in vacuo affords 0.37 g (91%) of the title compound as a white solid. (+)-APCI-MS: 381 (MH+).

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-cd33e0c4c67d49169fec5f0c4c6451bb
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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