反应详情

To a solution of 1.78 g (15.8 mmol) of potassium t-butoxide in 30 ml of THF, a solution of 3.28 g (15.8 mmol) of N-[bis(methylthio)methylene]glycine ethyl ester (Angew. Chem. Internat. Edit., 14, 426 (1975)) and 2.39 g (10.5 mmol) of 3-t-butylbenzyl bromide (Eur. J. Med. Chem., 23, 477 (1988)) in 10 ml of THF was added at −78° C. and the mixture was stirred at room temperature for 1 hour. Under cooling with ice, 10 ml of water was added, then 5 ml of 2 N aqueous sodium hydroxide was added and the mixture was stirred at room temperature for another 1 hour. Under cooling with ice, 2 N hydrochloric acid was added to the reaction mixture to render it acidic; the reaction mixture was extracted with chloroform and washed first with water, then with saturated brine. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate) to give N-[bis(methylthio)methylene]-3-t-butylphenylalanine in the amount of 577 mg (16%).

1. additionwas added
2. stirringthe mixture was stirred at room temperature for another 1 hour
3. additionwas added to the reaction mixture
4. extractionthe reaction mixture was extracted with chloroform
5. washwashed first with water
6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate)