Iodoethane → [5-(3,5-Difluorophenyl)-5-methyl-2,4-dioxo-3-ethylimidazolidin-1-yl]acetic acid

Participants

Reaction Steps

To a stirred solution of ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxoimidazolidin-1-yl]acetate, isomer A from Step D (50.0 mg, 0.160 mmol) in DMF (1 mL) was added potassium carbonate (33.0 mg, 0.192 mmol) and iodoethane (0.015 mL, 0.192 mmol). The reaction was stirred at ambient temperature for 18 h and then a solution of 1 N NaOH (0.480 mL, 0.480 mmol) was added and stirring continued for 3 h. The reaction mixture was diluted with DMSO (1 mL), filtered, and purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the racemic title compound. MS: m/z=313 (M+1).

Provenance & Evidence