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

HRID 543594Notes

Reaction equation

HRID 543594 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 1 N sodium hydroxide solution in an ice bath. The reaction mixture is stirred for 30 minutes at room temperature, acidified with 2 N 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-71389deae0534ceba6175e7dcc07b3ae
Source dataset
uspto-grants-1984_05
Patent number
US04447360

Reaction notes

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