L-Alanine → (S)-2-(2,6-dinitrobenzamido)propanoic acid

Participants

Reaction Steps

The reaction of 2,6-dinitrobenzoyl chloride (prepared from 2,6-dinitrobenzoic acid, 1 g and SOCl2, 10 mL) with L-alanine (0.52 g, 5.895 mmol) in the presence of Na2CO3 (0.625 g, 5.895 mmol) as described in intermediate 2 gave the title compound as a pale brown color solid (1.06 g, 80%), mp 222-224° C. 1H NMR (400 MHz, DMSO-d6): δ 12.81 (1H, br s), 9.23 (1H, d, J=7.6 Hz), 8.45 (2H, d, J=8.4 Hz), 7.92 (1H, t, J=8.2 Hz), 4.47 (1H, pentet, J=7.2 Hz), 1.33 (3H, d, J=7.2 Hz); LC-MS (negative ion mode): m/z 282 (M−H)−.

Provenance & Evidence