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

HRID 425375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425375
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

Komponenten

4

Edukt 2

HCID 10387Benzyl chloroformateHCID 856814-Bromophenylalanine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e0dd7a8f33f24837b0f864417f743144
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106070B2

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