Ketoprofen → HCID 86623049, compound

Participants

Reaction Steps

Boc-amino-1,5-pentanediol (Boc-NHCH(CH2OH)CH2CH2CH2OH, manufactured by Aldrich Chem. Co.) (1.98 mmol) was dissolved in dichloromethane (2 ml), and a dichloromethane solution (4 ml) of ketoprofen (3.96 mmol) (manufactured by Tokyo Kasei Kogyo) and a dichloromethane solution (1 ml) of DMAP (0.791 mmol) were added thereto in this order, followed by stirring. The reaction solution was ice-cooled, and a dichloromethane solution (5 ml) of WSCI.HCl (4.93 mmol) was added thereto, followed by stirring overnight while gradually returning to room temperature. The reaction solution was diluted with ethyl acetate, washed with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively, followed by dehydration drying with sodium sulfate, and then the solvent was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:2, 0.5% triethylamine) to give the titled compound (1.361 g, yield 99%). The structure was identified by 1H-NMR (CDCl3).

Provenance & Evidence