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

HRID 1248421Notes

Reaction equation

HRID 1248421 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].[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

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°.

Workup

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

Sources & evidence

ORD record
ord-c77318d03e0c4f1aa2e90346e137053f
Source dataset
uspto-grants-1985_06
Patent number
US04524028

Reaction notes

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