N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t-butylester → N-[1-(S)-ethoxycarbonyl-3-phenyl-3(R)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester

HRID 4367Notes

Reaction equation

HRID 4367 reaction equation
[C:1]([O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:31])[C@H:13]([CH3:30])[NH:14][C@H:15]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:31])[C@H:13]([CH3:30])[NH:14][C@H:15]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:16][C@H:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:18])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 14452797N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t-butylester

Product 1

HCID 18611612N-[1-(S)-ethoxycarbonyl-3-phenyl-3(R)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

13.4 g (30 mmoles) of N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t - butylester are dissolved in 120 ml of ethanol and hydrogenated in the presence of 1.5 g of 10% palladium-on-charcoal catalyst at room temperature. After the uptake of the theoretically needed hydrogen (720 ml), the catalyst is filtered off. A mixture of N-[1-(S)-ethoxycarbonyl-3-phenyl-3(S)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester and N-[1-(S)-ethoxycarbonyl-3-phenyl-3(R)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester is obtained.

Workup

  1. filtrationAfter the uptake of the theoretically needed hydrogen (720 ml), the catalyst is filtered off
  2. additionA mixture of N-[1-(S)-ethoxycarbonyl-3-phenyl-3(S)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester

Sources & evidence

ORD record
ord-10bcb14ff2a94443b04413a0a391e4dc
Source dataset
uspto-grants-1988_02
Patent number
US04725617

Reaction notes

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