Hydrochloric Acid → HCID 86757100, compound

Participants

Reaction Steps

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%).

Provenance & Evidence