Methanol → HCID 18626613, compound

Participants

Reaction Steps

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester and 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid ethyl ester (268 mg) and methyl urea (110 mg, 1.5 mmol) in magnesium methoxide in methanol (7.4 wt %, 1.6 mL, 1.1 mmol) was heated to 100° C. for 8 h. At this time, the reaction was concentrated in vacuo. The residue was then dissolved in ethyl acetate (50 mL), filtered through a plug of silica gel, and washed with ethyl acetate (100 mL). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) afforded 1-[2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (55 mg, 19% yield) as a white foam: FAB-HRMS m/e calcd for C17H23ClN2O4S (M+H)+387.1145, found 387.1156.

Provenance & Evidence