Triethylamine → Benzyl 2-(2-chloro-5-nitrobenzamido)acetate

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Reaction Steps

The reaction of 2-chloro-5-nitrobenzoyl chloride (prepared from 2-chloro-5-nitrobenzoic acid, 1.0 g and SOCl2, 10 mL) with benzyl glycinate.PTS salt (1.9 g, 5.9 mmol) in the presence of triethylamine (2.0 mL, 14.88 mmol) as described in intermediate 1 gave the title compound as a colorless solid (1.42 g, 82%), mp 116-118° C. 1H NMR (400 MHz, CDCl3): δ 8.54 (1H, d, J=2.8 Hz), 8.23 (1H, dd, J=8.6, 2.6 Hz), 7.61 (1H, d, J=8.8 Hz), 7.38 (5H, br s), 6.88 (1H, br s), 5.24 (2H, s), 4.32 (2H, d, J=4.8 Hz); LC-MS (positive ion mode): m/z 349, 351 (M+H)+.

Provenance & Evidence