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. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1, by volume) to obtain 0.25 g of N-[2-(1-Naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-L-histidine methyl ester having an Rf2 value of 0.56 as a white powder.

Provenance & Evidence