Hydrochloric Acid → N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-L-alanyl-L-proline, t-butyl ester, hydrochloride

HRID 1583682Notes

Reaction equation

HRID 1583682 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:10]([OH:39])[CH2:11][N:12](C(OCC1C=CC=CC=1)=O)[C@H:13]([C:15]([N:17]1[CH2:28][CH2:27][CH2:26][C@H:18]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:47]>CO.[Pd]>[ClH:47].[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:10]([OH:39])[CH2:11][NH:12][C@H:13]([C:15]([N:17]1[CH2:28][CH2:27][CH2:26][C@H:18]1[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[O:16])[CH3:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131714416(3S)-1-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, t-butyl ester

Product 1

HCID 131714418N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-L-alanyl-L-proline, t-butyl ester, hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(3S)-1-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, t-butyl ester (550 mg, 0.86 mmol) was dissolved in methanol (35 ml) and hydrochloric acid (1N, 0.86 ml). Palladium on carbon catalyst (10%, 200 mg) was added and the solution was stirred under an atmosphere of hydrogen overnight, filtered through Hyflo and evaporated yielding 450 mg of the title compound.

Workup

  1. filtrationfiltered through Hyflo
  2. customevaporated

Sources & evidence

ORD record
ord-033631feb4df411e9152f8d3d8d827a1
Source dataset
uspto-grants-1985_11
Patent number
US04552866

Reaction notes

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