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

HRID 1861598Notes

Reaction equation

HRID 1861598 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(=O)(O)[O-].[Na+].O>CC(C)=O>[CH2:1]([O:8][C:9]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of benzylchloroformate (9.4 g, 5.5 mmol) in acetone (15 ml) was added dropwise to a mixture of 4-aminobutanoic acid (5.2 g, 5 mmol), sodium bicarbonate (8.6 g, 10 mmol), water (25 ml) and acetone (25 ml) causing vigorous effervescence. The solution was allowed to stir overnight. The acetone was removed using a rotary evaporator to leave an aqueous phase which was washed with ether (2×25 ml). The resulting aqueous layer was acidified to pH2 with dilute hydrochloric acid and then extracted with dichloromethane (3×50 ml). The dichloromethane extracts were combined, dried over magnesium sulphate and volatile components removed under reduced pressure to leave 4-[(benzyloxycarbonyl)amino]butanoic acid as a white solid in a good state of purity. This material was used without further purification.

Workup

  1. customThe acetone was removed
  2. customa rotary evaporator
  3. customto leave an aqueous phase which
  4. washwas washed with ether (2×25 ml)
  5. extractionextracted with dichloromethane (3×50 ml)
  6. dry with materialdried over magnesium sulphate and volatile components
  7. customremoved under reduced pressure

Sources & evidence

ORD record
ord-b4a092e576844b9e8acf7be42d2fcc8c
Source dataset
uspto-grants-2003_03
Patent number
US06534488B1

Reaction notes

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