Sodium Carbonate → (R)-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 D-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 (2.18 g, 82%), mp 192-194° C. 1H NMR (400 MHz, DMSO-d6): δ 12.92 (1H, br s), 9.32 (1H, d, J=7.2 Hz), 8.83 (1H, d, J=1.6 Hz), 8.69 (1H, dd, J=8.2, 1.4 Hz), 7.93 (1H, d, J=8.4 Hz), 4.49 (1H, pentet, J=7.2 Hz), 1.44 (3H, d, J=7.2 Hz); LC-MS (negative ion mode): m/z 282 (M−H)−.

Provenance & Evidence