Methanol → 1-{2-(3,4-Dichloro-phenyl)-3-[3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionyl}-3-methyl-urea

Participants

Reaction Conditions

Reaction Steps

2-(3,4-Dichloro-phenyl)-3-[3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester (1.60 mg, 3.98 mmol) and methylurea (443 mg, 5.98 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. %, 11.4 mL, 7.97 mmol) was heated under reflux at 100° C. for 18 h. The reaction mixture was then concentrated in vacuo and filtered through a plug of celite (100% ethyl acetate as eluent). Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50/50 hexanes/ethyl acetate) afforded 1-{2-(3,4-dichloro-phenyl)-3-[3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionyl}-3-methyl-urea (160.6 mg, 9.1%) as a white solid: mp 62–65° C.; FAB-HRMS m/e calcd for C21H28Cl2N2O4 (M+Na)+ 465.1324, found 465.1324.

Provenance & Evidence