HCID 70041394, compound → HCID 70043572, compound

HRID 742859Notes

Reaction equation

HRID 742859 reaction equation
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:21]([OH:38])[CH2:22][N:23]1[C@H:27]([C:28]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][C@@H:25]2[CH2:35][CH2:36][CH2:37][C@H:24]12)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:21]([OH:38])[CH2:22][N:23]1[C@H:27]([C:28]([NH:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:26][C@@H:25]2[CH2:35][CH2:36][CH2:37][C@H:24]12)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15]

Participants

4

Reactant 1

HCID 70041394HCID 70041394, compound

Product 1

HCID 70043572HCID 70043572, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 397 mg of 1-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-(3aS,6aS)-cyclopenta[b]pyrrole-2(S)-carboxamide in 20 ml of ethanol was hydrogenated over 10% palladium-on-carbon at 20° C. and under atmospheric pressure for 4 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 312 mg of 1-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-(3aS,6aS)-cyclopenta[b]pyrrole-2(S)-carboxamide as a pale yellow gum; MS: m/e 488 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9b34cb41b80746598aa9a33e56cbbf5f
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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