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

HRID 1881456Notes

Reaction equation

HRID 1881456 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-7e5da768403e433fa6197204845787f8
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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