Methanol → 1-[2-(4-Cyano-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea

Participants

Reaction Steps

A mixture of 2-(4-cyano-phenyl)-3-cyclopentyl-propionic acid methyl ester (257 mg, 1.0 mmol) and methyl urea (148 mg, 2.0 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 2.0 mL, 1.40 mmol) was heated to reflux for 48 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 70/30 ethyl acetate/hexanes) afforded 1-[2-(4-cyano-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (48.8 mg, 16.3%) as a white solid: mp 61-65° C.; FAB-HRMS m/e calcd for C17H21N3O2 (M+H)+300.1712 found 300.1722.

Provenance & Evidence