Ketoprofen → HCID 86623052, compound

Participants

Reaction Steps

Boc-amino-1,2-propanediol (Boc-NHCH2CH(OH)CH2OH, manufactured by Aldrich Chem. Co.) (2.05 mmol) was dissolved in dichloromethane (2 ml), and a dichloromethane solution (4 ml) of ketoprofen (4.11 mmol) (manufactured by Tokyo Kasei Kogyo) and a dichloromethane solution (1 ml) of DMAP (0.803 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 (4.94 mmol) was added thereto, followed by stirring overnight while gradually returning to room temperature. The reaction solution was ice-cooled, and a dichloromethane solution (1 ml) of WSCI.HCl (1.24 mmol) was added thereto, followed by stirring at room temperature for 1 hour and then at 35° C. for 2 hours. Ethyl acetate was added thereto, followed by washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively. Dehydration drying with sodium sulfate was carried out, and then the solvent was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1, 0.5% triethylamine) to give the titled compound (1.175 g, yield 87%). The structure was identified by 1H-NMR (CDCl3).

Provenance & Evidence