Hydrochloric Acid → (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid

Participants

Reaction Conditions

Reaction Steps

To (4R)-4-(3-bromo-4-chlorophenyl)pyrrolidin-2-one (0.2 g, 0.73 mmol) was added 0.2 mL acetonitrile and 1 mL 6N HCl aqueous solution. The mixture was heated overnight at 95° C. The reaction mixture was then cooled to room temperature and neutralized with a 4N NaOH aqueous solution. The mixture was purified by reversed phase LC/MS to provide (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid (43 mg, 30% yield), which was then converted to the title compound as the hydrochloride salt by lyophilization from a 1N HCl aqueous solution. 1H-NMR (400 MHz, CD3OD): δ 7.68-7.69 d, J=2.00 Hz, 1H), 7.51-7.53 (d, J=8.44 Hz, 1H), 7.30-7.33 (dd, J=8.4, 2.44 Hz, 1H), 3.32-3.40 (m, 2H), 3.15-3.21 (m, 1H), 2.77-2.83 (dd, J=16.8, 6.4, 4 Hz, 1H), 2.63-2.69 (dd, J=16.4, 7.66 Hz, 1H); MS (ESI) m/z 293.89 (M+H)+.

Provenance & Evidence