Triethylamine → HCID 178501430, compound

Participants

Reaction Conditions

Reaction Steps

In 200 ml of dry chloroform was suspended 10.0 g of L-histidine methyl ester dihydrochloride, and to the suspension were successively added 18.4 ml of triethylamine and 10.2 g of 4-methoxybenzyloxycarbonylazide under cooling. The mixture was stirred for 16 hours at 0° C., and then the reaction mixture was evaporated under reduced pressure. To the residue was added a 5% aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. 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 flash column chromatography (eluent: chloroform/methanol=10/1) to obtain 11.0 g of N-(4-methoxybenzyloxycarbonyl)-L-histidine methyl ester as a yellow oil. In 112 ml of methanol was dissolved 10.9 g of the ester compound obtained, and to the solution was added 9.9 ml of hydrazine monohydrate. The mixture was stirred for 4 hours at room temperature, and then the reaction mixture was evaporated under reduced pressure. The residue was washed with ethanol and then dried at below 40° C. to obtain 4.9 g of N-(4-methoxybenzyloxycarbonyl)-L-histidine hydrazide as a white powder.

Provenance & Evidence