L-Alanine → Propanoic acid, 2-(acetyloxy)-, (2R)-

Participants

Reaction Steps

To a solution of (S)-2-aminopropanoic acid (60 g, 0.67 mol) in acetic acid (400 ml) was added NaNO2 (93 g, 1.34 mol) several portions at 0° C. After addition, the mixture was stirred at room temperature for 4 hours. After removed the acetic acid, water added and then extracted with ether. The organic phase was collected, dried, concentrated to afford (R)-2-acetoxypropanoic acid (30 g, 35%). 1H NMR (400 MHz, CDCl3) δ ppm, 11.70 (s, 2H), 5.02-5.07 (q, 1H), 2.07 (s, 3H), 1.46-1.52 (d, 3H).

Provenance & Evidence