Ethyl (2S)-2-benzamido-3-(4-nitrophenyl)propanoate → 4-Amino-N-benzoyl-L-phenylalanine ethyl ester

HRID 2229497Notes

Reaction equation

HRID 2229497 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C@@H:5]([NH:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[C@@H:5]([NH:16][C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 9840971Ethyl (2S)-2-benzamido-3-(4-nitrophenyl)propanoate

Product 1

HCID 544765864-Amino-N-benzoyl-L-phenylalanine ethyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-Ethyl-2-benzoylamino-3-(4-nitrophenyl)propionate (0.542 g, 1.58 mmol) was dissolved with warming in EtOH (20 mL) and to the cooled solution was added 10% Pd/C (0.108 g, 20% w/w). The mixture was stirred overnight at room temperature under a balloon of H2. The mixture was filtered through a pad of celite and the filtrate was concentrated to an off-white solid and flash chromatographed (silica gel, 1:1 hexanes:EtOAc) to afford the title compound as a white solid (0.323 g, 66%).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated to an off-white solid and flash
  3. customchromatographed (silica gel, 1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-2f72b837c43f4dd386fa0ad8b6526666
Source dataset
uspto-grants-2002_07
Patent number
US06420424B1

Reaction notes

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