Benzyl chloroformate → (3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone

HRID 1071879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071879
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4](=[O:7])[CH2:5][Cl:6].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(=O)([O-])O.[Na+]>O.C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16]([NH:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4](=[O:7])[CH2:5][Cl:6])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 56777393(S)-3-Amino-1-chloro-4-phenylbutan-2-one hydrochloride

Produkt 1

HCID 99625(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanoneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

(3S)-3-Amino-1-chloro-4-phenyl-2-butanone hydrochloride (100 mg) was dissolved in water (4.3 ml). A solution (5.3 ml) of benzyl chloroformate (0.794 ml) in toluene was added to the obtained solution. Further, an aqueous solution (1.0 ml) of sodium hydrogencarbonate (71.9 mg) was added dropwise to the obtained mixture. They were stirred at room temperature for 50 minutes to conduct the reaction and then the aqueous layer was separated. The obtained toluene layer was analyzed by HPLC to find that (3S)-3-benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone (118 mg) was obtained in a yield of 83%.

Aufarbeitung

  1. customthe reaction
  2. customthe aqueous layer was separated
  3. customwas obtained in a yield of 83%

Quellen und Nachweise

ORD-Eintrag
ord-93091396635448b590308df7d47a2b40
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906224B2

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