L-Alanine → (S)-2-(2,4-dinitrobenzamido)propanoic acid

Participants

Reaction Steps

The reaction of 2,4-dinitrobenzoyl chloride (prepared from 2,4-dinitrobenzoic acid, 2 g and SOCl2, 20 mL) with L-alanine (1.04 g, 11.79 mmol) in the presence of Na2CO3 (1.24 g, 11.79 mmol) as described in intermediate 2 gave the title compound as an off-white color solid (2.08 g, 78%), mp 194-196° C. 1H NMR (400 MHz, DMSO-d6): δ 12.77 (1H, s), 9.25 (1H, d, J=7.6 Hz), 8.77 (1H, d, J=2.0 Hz), 8.63 (1H, dd, J=8.4, 2.0 Hz), 7.87 (1H, d, J=8.4 Hz), 4.44 (1H, pentet, J=7.3 Hz), 1.38 (3H, d, J=7.2 Hz); LC-MS (negative ion mode): m/z 282 (M−H)−.

Provenance & Evidence