Gamma-Aminobutyric Acid → 4-(((Benzyloxy)carbonyl)amino)butanoic acid

HRID 462921

Reaktionsgleichung

Reaktionsgleichung von HRID 462921
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].Cl>O1CCOCC1.[OH-].[Na+]>[CH2:5]([O:4][C:2]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 10387Benzyl chloroformate

Produkt 1

HCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 5.16 g (0.103 mmol) of benzyl chloroformate in 100 ml of dry dioxan is added dropwise over a period of 30 minutes to a solution of 10.60 g (0.1 mmol) of 4-aminobutyric acid in 300 ml of 1N sodium hydroxide solution in an ice bath. The reaction mixture is stirred for 30 minutes at room temperature, acidified with 2N hydrochloric acid and extracted with methylene chloride. The organic phase is dried with sodium sulphate and concentrated in vacuo. The 4-benzyloxycarbonylaminobutyric acid obtained is recrystallised from ethyl acetate, methylene chloride and hexane; melting point 61°-62°.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase is dried with sodium sulphate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ea61c5728c944f2aa507a1acd9a10a35
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518533

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