Triethylamine → HCID 131728632, compound

Participants

Reaction Steps

In 1 ml of chloroform, 133 mg (0.76 mmol) of Boc-glycine was dissolved, and 106 μl (0.76 mmol) of triethylamine and Mpt-Cl 98 mg (0.76 mmol)/1 ml chloroform were added thereto under ice-cooling, followed by stirring for 10 minutes. Thereafter, 433 mg (0.5 mmol) of the tris(hydroxymethyl)aminomethane-ketoprofen hydrochloride obtained in Example 31/70 μl (0.5 mmol) of triethylamine/2 ml of chloroform, and 106 μl (0.76 mmol) of triethylamine were gradually added thereto by dividing into 4 portions. After stirring at room temperature for 1 hour, 106 μl (0.76 mmol) of triethylamine was further added thereto under ice-cooling, and a mixed acid anhydride of Boc-glycine activated by dissolving 131 mg (0.75 mmol) of Boc-glycine in 1 ml chloroform and by adding, under ice-cooling, 105 μl (0.75 mmol) of triethylamine and 95 mg (0.75 mmol) Mpt-Cl/1 ml chloroform was added thereto, and the mixture was stirred at room temperature overnight. Ethyl acetate was added thereto, followed by separation by washing twice with 5% citric acid, water, twice with 5% sodium hydrogen carbonate, water and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give 411 mg of the titled compound (yield 55%). The structure was identified by 1H-NMR (CDCl3).

Provenance & Evidence