Aspirin → Boc-aminopropanol acetylsalicylic Acid

Participants

Reaction Steps

Boc-aminopropanol (2.11 mmol), acetylsalicylic acid (2.11 mmol) (manufactured by Wako Pure Chemical Industries) and DMAP (0.42 mmol) were dissolved in dichloromethane-dioxane (2:1, 6 ml), and WSCI.HCl (2.35 mmol) was added thereto under ice-cooling. After returning to room temperature and stirring overnight, ethyl acetate was added thereto, followed by separation by washing with 5% citric acid, 5% sodium hydrogen carbonate and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 0.5% triethylamine) to give the titled compound (298.0 mg, yield 48%). The structure was identified by 1H-NMR (CDCl3).

Provenance & Evidence