Methanol → 1-[3-Cyclopentyl-2-(3-fluoro4-methanesulfonyl-phenyl)-propionyl]-3-methyl-urea

Participants

Reaction Conditions

Reaction Steps

3-Cyclopentyl-2-(3-fluoro-4-methanesulfonyl-phenyl)-propionic acid methyl ester (90 mg, 0.274 mmol) and methyl urea (61 mg, 0.822 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 1.0 mL, 0.685 mmol). The reaction mixture was then concentrated in vacuo to approximately one-half the volume of methanol. The resulting reaction mixture was then heated under reflux for 24 h. The resulting cloudy, white reaction mixture was allowed to cool to 25° C. and then filtered through celite. The celite was thoroughly washed with ethyl acetate. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(3-fluoro4-methanesulfonyl-phenyl)-propionyl]-3-methyl-urea (23.3 mg, 23%) as a white solid: mp 199-200° C.; EI-HRMS m/e calcd for C17H23FN2O4S (M+) 370.1362, found 370.1370.

Provenance & Evidence