(S)-(+)-4-Amino-3-hydroxybutanoic acid

Chemical Properties

Uses

General Description

Synthesis

1431373-89-5

7013-05-0

GENERAL METHODS: Compound 7 (400 mg, 0.92 mmol) was dissolved in EtOAc (20 mL) and 10% Pd/C (785 mg, 0.74 mmol, 80 mol%) was added. The reaction system was degassed and hydrogenated under 1 atm H2 atmosphere for 12 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford (S)-(+)-4-amino-3-hydroxybutyric acid ((S)-GABOB, 2) (95 mg, 87% yield) as a white solid. The product was purified by recrystallization from EtOH-H2O mixed solvent. Melting point: 200-202°C (literature value 13e: 198-201°C); [α]27D +17.2 (c 1.23, H2O) (literature value 13e: [α]25D +16.7 (c 0.41, H2O)).1H NMR (600 MHz, D2O): δ 2.44 (d, J = 6.6 Hz, 2H), 3.97 (dd J = 13.2, 9.6 Hz, 1H), 3.18 (dd, J = 13.2, 3.0 Hz, 1H), 4.19-4.23 (m, 1H). 13C NMR (150 MHz, D2O): δ 42.3, 44.1, 65.5, 178.6. HRMS (ESI): m/z [M + Na]+ calculated value C4H9NNaO3: 142.0480; measured value: 142.0462. ref 22: Abdel-Magid, A. F.; Carson, K.

References