Hydrochloric Acid → HCID 13933332, compound

HRID 652345Notes

Reaction equation

HRID 652345 reaction equation
C1(COC([NH:11][C@@H:12]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:13]([OH:34])[CH2:14][NH:15][C@H:16]([C:24]([O:26]CC2C=CC=CC=2)=[O:25])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)C=CC=CC=1.[ClH:42]>C(O)C.[Pd]>[ClH:42].[ClH:42].[NH2:11][C@@H:12]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:13]([OH:34])[CH2:14][NH:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131714413HCID 131714413, compound

Product 1

HCID 13933332HCID 13933332, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[(3S)-3-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-L-phenylalanine, phenylmethyl ester (1.14 g, 2.06 mmol) in 30 ml of 95% ethanol was added 4.2 ml of lN hydrogen chloride and 250 mg of 10% palladium on carbon catalyst. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen. A white precipitate which separated upon addition of the aqueous hydrogen chloride redissolved as the reaction proceeded. After 17 hours, the catalyst was filtered and the solvent was evaporated. Trituration with methanolether afforded 531 mg of the title compound as a white solid, melting point 147-163° C. The 1H-NMR showed an approximately 1:1 mixture of alcohol isomers. Evaporation of the filtrate from the trituration gave 0.21 g of material which was enriched in one of the diastereomers.

Workup

  1. customA white precipitate which separated upon addition of the aqueous hydrogen chloride
  2. dissolutionredissolved as the reaction
  3. filtrationthe catalyst was filtered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-630a35d98e5a434eaf405a68b5e50751
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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