Methanol → HCID 10294433, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid methyl ester (196.5 mg, 0.548 mmol) and methyl urea (121.8 mg, 1.64 mmol) was treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 3.1 mL, 2.19 mmol). The resulting reaction mixture was then heated under reflux for 24 h. The reaction mixture was allowed to cool to 25° C. and then filtered through celite. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 9/1 hexanes/ethyl acetate then 3/1 to 1/1 hexanes/ethyl acetate gradient elution) afforded 1-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionyl]-3-methyl urea (76.9 mg, 35%) as a white foam: mp 85-88° C.; EI-HRMS m/e calcd for C26H28N2O2 (M+) 400.2151, found 400.2150.

Provenance & Evidence