Methanol → 1-(2-Biphenyl-4-yl-3-cyclopentyl-propionyl)-3-methyl urea

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester (987.4 mg, 3.20 mmol) and methyl urea (948.7 mg, 12.80 mmol) was treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 18 mL, 12.80 mmol). The resulting reaction mixture was then heated under reflux for 19 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, 3/1 hexanes/ethyl acetate) afforded 1-(2-biphenyl-4-yl-3-cyclopentyl-propionyl)-3-methyl urea (152.5 mg, 14%) as a white solid: mp 195-197° C.; EI-HRMS m/e calcd for C22H26N2O2 (M+) 350.1994, found 350.2004.

Provenance & Evidence