Gamma-Aminobutyric Acid → HCID 16772272, compound

To a solution of 20 gm (194 mMol) 4-aminobutanoic acid in dichloromethane (700 ml) were added 54 ml (407 mMol) triethylamine and the reaction mixture was stirred at room temperature for 10 minutes. To this mixture was then added a solution of 40.6 ml (407 mMol) isobutyryl chloride in dichloromethane (300 ml) dropwise and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in 1N sodium hydroxide and stirred for 30 minutes. This solution was then poured into diethyl ether, diluted with water and the phases separated. The aqueous phase was acidified with hydrochloric acid and then extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate and concentrated under reduced pressure to give an oil. Bulb to bulb distillation (0.05 mm Hg, pot temperature=235° C.) gave 13.98 gm (43.1%) N-(2-methyl)propionyl-4-aminobutanoic acid.

1. stirringthe resulting mixture was stirred at room temperature for 2 hours
2. filtrationThe reaction mixture was filtered
3. concentrationthe filtrate concentrated under reduced pressure
4. dissolutionThe residue was dissolved in 1N sodium hydroxide
5. stirringstirred for 30 minutes
6. additionThis solution was then poured into diethyl ether
7. additiondiluted with water
8. customthe phases separated
9. extractionextracted with ethyl acetate
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. customto give an oil
13. distillationBulb to bulb distillation (0.05 mm Hg, pot temperature=235° C.)

ORD record

ord-8ba1d4f18b694e18bfe00cbdca6132af

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05270328