(R)-2-(2-Fluoro-6-nitrobenzamido)propanoic acid → (R)-2-(2-Amino-6-fluorobenzamido)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of iron powder (1.3 g, 23.42 mmol) in AcOH (12 mL) was added (R)-2-(2-fluoro-6-nitrobenzamido)-propanoic acid (600 mg, 2.34 mmol) at rt and stirred at 60-70° C. for 30 min. Work-up of the reaction mixture as described in example 6 gave the product as an off-white color solid (380 mg, 72%), mp 220-224° C. 1H NMR (400 MHz, DMSO-d6): δ 12.67 (1H, br s), 8.46 (1H, d, J=5.2 Hz), 7.08 (1H, dd, J=14.8, 7.2 Hz), 6.50 (1H, d, J=8.0 Hz), 6.31 (1H, t, J=9.2 Hz), 5.89 (2H, br s), 4.37 (1H, pentet, J=7.2 Hz), 1.35 (3H, d, J=7.2 Hz); LC-MS (positive ion mode): m/z 227 (M+H)+.

Provenance & Evidence