Mefenamic Acid → HCID 86623038, compound

Participants

Reaction Steps

Boc-aminopropanol (0.616 mmol), mefenamic acid (0.620 mmol) (manufactured by Wako Pure Chemical Industries) and DMAP (0.126 mmol) were dissolved in dichloromethane (3 ml), and a dichloromethane solution (1.5 ml) of WSCI.HCl (0.758 mmol) was added thereto, under ice-cooling. After gradually returning the reaction temperature to room temperature, the mixture was stirred overnight. The reaction solution was again ice-cooled, and a dichloromethane solution (1 ml) of WSCI.HCl (0.207 mmol) was added thereto, followed by stirring for 5 hours while gradually returning to room temperature. Ethyl acetate was added to the reaction solution, and the mixture was washed with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively. After dehydration drying with sodium sulfate, the solvent was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1, 0.5% triethylamine) to give the titled compound (190.4 mg, yield 78%). The structure was identified by 1H-NMR (CDCl3).

Provenance & Evidence