Benzyl chloroformate → 2-{[(Benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propanoic acid

HRID 425375Notes

Reaction equation

HRID 425375 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Br:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][CH:18]([C:20]([OH:22])=[O:21])[NH2:19])=[CH:15][CH:14]=1>C(OCC)(=O)C>[CH2:5]([O:4][C:2]([NH:19][CH:18]([CH2:17][C:16]1[CH:15]=[CH:14][C:13]([Br:12])=[CH:24][CH:23]=1)[C:20]([OH:22])=[O:21])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 856814-Bromophenylalanine

Product 1

HCID 220659152-{[(Benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloroformate (8.65 mL, 61.5 mmol) was added to a refluxing solution of 4-bromo-dl-phenylalanine (15 g, 61.5 mmol) in ethyl acetate (250 mL). After stirring at reflux overnight, the reaction mixture was cooled to ambient temperature, filtered through celite and concentrated in vacuo to afford 2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propanoic acid which was used in the subsequent step without further purification.

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0dd7a8f33f24837b0f864417f743144
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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