(R)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate → (2R)-2-amino-3-phenylpropanamide

HRID 84815

Reaction equation

HRID 84815 reaction equation
[NH2:1][C:2](=[O:22])[C@H:3]([NH:11]C(=O)OCC1C=CC=CC=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.[Pd]>[NH2:11][C@@H:3]([C:2]([NH2:1])=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 68077307(R)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

Product 1

HCID 7000171(2R)-2-amino-3-phenylpropanamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-benzyl 1-amino-1-oxo-3-phenylpropan-2-ylcarbamate (910 mg, 3.05 mmol) and Pd—C (10%, 200 mg) in MeOH (20 mL) was hydrogenated under balloon H2 for 16 h. It was filtered through celite. The filtrate was concentrated in vacuo to give D-phenylalanine amide as a white solid (493 mg).

Workup

  1. filtrationIt was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3a46015da6164ff6a39edee6f71e7158
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Linked notes

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