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

HRID 413989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413989
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-5c6d57d1703544d8b1b28c984328ce38
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06570039B2

Notizen zur Reaktion

Wird geladen…