L-Leucine → Leucic acid, L-

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of L-Leu-OH (5.0 g, 38.2 mmol) in 1 N H2SO4 (50 mL) at 0° C. was slowly added over 11/2 h a solution of sodium nitrite (NaNO2) (7.5 g, 0.11 mmol) in water (20 mL) while maintaining the temperature at 0° C. The reaction mixture was gradually warmed to R.T., stirred for 24 h, and concentrated to give a white solid. The solid was extracted with ether (5×50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give (2S)-2-hydroxy-4-methylpentanoic acid as an oil (4.1 g, 81.2%): 1H NMR (CDCl3, 300 MHz) δ0.98 (d, 6 H, J=12.0 Hz), 1.57-1.67 (m, 2 H), 1.82-1.93 (m, 1 H), 4.36 (t, 1 H, J=6.0 Hz) ppm.

Provenance & Evidence