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

Participants

Reaction Conditions

Reaction Steps

A mixture of spray-dried KF (1.02 g, 17.6 mmol), intermediate 13 (500 mg, 1.76 mmol) and catalytic amount of 18-crown-6 in dry DMSO (10 mL) was stirred at 170-180° C. for 45 min. Work-up of the reaction mixture as described in example 1 gave the product as a pale brown color solid (284 mg, 63%), mp 142-144° C. 1H NMR (400 MHz, DMSO-d6): δ 9.05 (1H, d, J=7.2 Hz), 8.01 (1H, dd, J=6.6, 1.8 Hz), 7.72-7.78 (2H, m), 4.44 (1H, pentet, J=7.2 Hz), 1.34 (3H, d, J=7.2 Hz); LC-MS (positive ion mode): m/z 279 (M+Na)+.

Provenance & Evidence