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

HRID 652348Notes

Reaction equation

HRID 652348 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-0f6bdff3ce03424f9b4c27cb1a686b88
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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