Triethylamine → HCID 178501404, compound

Participants

Reaction Steps

To a suspension of 0.89 g of 2-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionic acid and 0.79 g of L-histidine methyl ester dihydrochloride in 23 ml of N,N-dimethylformamide were added 0.70 ml of diphenylphosphoryl azide and 1.50 ml of triethylamine with stirring under ice-cooling, and then the mixture was additionaly stirred for 16 hours. The reaction mixture was evaporated under reduced pressure, and to the residue was added a 5% aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. To the residue was added diethyl ether, and the precipitate was collected by filtration to obtain 1.25 g of N-[2-(1-naphthylmethyl)-3 -(morpholinocarbonyl)propionyl]-L-histidine methyl ester as a white powder. To a soluiton of 0.98 g of the ester compound in 10 ml of methanol was added 0.52 g of hydrazide monohydrate, and then the mixture was stirred for 4 hours. The reaction mixture was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1 by volume) to obtain 0.23 g of N-[2-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-L-histidine hydrazide having an Rf1 value of 0.49 as a white powder.

Provenance & Evidence