Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 1-[2-(3,4-Dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionyl]-3-methyl-urea

Participants

Reaction Conditions

Reaction Steps

A solution of 1-{2-(3,4-dichloro-phenyl)-3-[3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionyl}-3-methyl-urea (150.7 mg, 0.33 mmol) in ethanol (3.4 mL) was treated with pyridinium p-toluenesulfonate (8.54 mg, 0.03 mmol). The reaction mixture was heated to 60° C. for 18 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230400 mesh, 80/20 methylene chloride/methanol) afforded 1-[2-(3,4-dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionyl]-3-methyl-urea (102.2 mg, 83.7%) as a white solid: mp 82–84° C.; FAB-HRMS m/e calcd for C16H20Cl2N2O3 (M+H)+ 359.0929, found 359.0936.

Provenance & Evidence