18-Crown-6 → (R)-2-(2-Fluoro-4-nitrobenzamido)propanoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of spray-dried KF (307 mg, 5.3 mmol), intermediate 12 (150 mg, 0.53 mmol) and catalytic amount of 18-crown-6 in dry DMSO (4 mL) was stirred at 170-180° C. for 30 min. Work-up of the reaction mixture as described in example 1 gave the product as a pale brown color solid (92 mg, 68%), mp 146-150° C. 1H NMR (400 MHz, DMSO-d6): δ 8.90 (1H, d, J=4.0 Hz), 8.21 (1H, d, J=9.6 Hz), 8.15 (1H, d, J=8.0 Hz), 7.84 (1H, t, J=6.8 Hz), 4.36-4.40 (1H, m), 1.38 (3H, d, J=6.4 Hz); LC-MS (negative ion mode): m/z 255 (M−H)−.

Provenance & Evidence