(S)-N-(Phenylmethyl)-2-[[(S)-2-[(phenylmethyloxy)acetyl]-1-pyrrolidinyl]carbonyl]-1-pyrrolidinecarboxamide → Jtp-4819

HRID 1735403Notes

Reaction equation

HRID 1735403 reaction equation
[C:1]1([CH2:7][NH:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[C:16]([N:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23](=[O:33])[CH2:24][O:25]CC2C=CC=CC=2)=[O:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.O.C(O)(=O)C.[Pd]>[OH:25][CH2:24][C:23]([C@@H:19]1[CH2:20][CH2:21][CH2:22][N:18]1[C:16]([C@@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]([NH:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10])=[O:17])=[O:33]

Participants

6

Reactant 1

HCID 54369562(S)-N-(Phenylmethyl)-2-[[(S)-2-[(phenylmethyloxy)acetyl]-1-pyrrolidinyl]carbonyl]-1-pyrrolidinecarboxamide

Product 1

HCID 178060Jtp-4819Yield 80.7%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(S)-N-(Phenylmethyl)-2-[[(S)-2-[(phenylmethyloxy)acetyl]-1-pyrrolidinyl]carbonyl]-1-pyrrolidinecarboxamide (40.0 g) was dissolved in a mixed solvent of methanol (200 ml), water (40 ml) and acetic acid (20 ml). Palladium-black (4.0 g) was added and the mixture was stirred at room temperature under a hydrogen atmosphere for 3.5 hours. The catalyst in the reaction mixture was filtered off and the filtrate was concentrated to give the title compound (25.8 g).

Workup

  1. filtrationThe catalyst in the reaction mixture was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2262970c19a5420189c7e49293dabb14
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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