Methanol → 3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cylopentyl-2-(4-phenoxy-phenyl)-propionic acid (200 mg, 0.64 mmol) in methylene chloride (10 mL) with one drop of N,N-dimethylformamide was cooled to 0° C. under a nitrogen atmosphere. The reaction mixture was then treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.48 mL, 0.97 mmol), and the resulting reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was then treated with 1,1,1,3,3,3-hexamethyldisilazane (0.47 mL, 2.24 mmol) and then allowed to warm to 25° C. where it was stirred for 16 h. After such time, the reaction mixture was treated with methanol (10 mL) and then allowed to stir at 25° C. for 10 min. The resulting reaction mixture was washed with a 5% aqueous sulfuric acid solution (2×10 mL). The combined aqueous extracts were further extracted with methylene chloride (2×10 mL). The combined organic extracts were then washed with a saturated aqueous sodium chloride solution (1×10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-phenoxy-phenyl)-propionamide (120 mg, 61%,) as a white solid: mp 91.6-94.4° C.; EI-HRMS m/e calcd for C20H23NO2 (M+) 309.1729, found 309.1733.

Provenance & Evidence