Methanol → HCID 18626646, compound

Participants

Reaction Conditions

Reaction Steps

3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid methyl ester (350 mg, 1.13 mmol) and methyl urea (184 mg, 2.48 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 6.0 mL, 4.18 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 15 h. The reaction mixture was allowed to cool to 25° C., filtered through celite, and the celite was thoroughly washed with ethyl acetate. The ethyl acetate filtrate was washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/3 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionyl]-3-methyl urea (124 mg, 31%) as a white solid: mp 205-206° C.; EI-HRMS m/e calcd for C17H24N2O4S (M+) 352.1457, found 352.1445.

Provenance & Evidence