Triethylamine → HCID 19790977, compound

Participants

Reaction Steps

To a suspension of 7.68 g of β-alanine ethyl ester hydrochloride in 50 ml of methylene chloride there was added, with stirring, 5.56 g of triethyl- amine. 10.86 g of N-t-butoxycarbonyl-5-aminovaleric acid, dissolved in 50 ml of methylene chloride, and portionwise 11.35 g of DCC, in that order. After completion of the addition, the reaction mixture was stirred at room temperature overnight and filtered off from separated urea. The filtrate was washed in succession with 250 ml of sodium bicarbonate solution (5%), water, 250 ml of 0.1M citric acid and, finally, with saturated sodium chloride solution. Thereafter, the solvent was evaporated under reduced pressure and the oily residue was purified by column chromatography on silica gel, to obtain N-[5-(1-t-butoxyformamido)valeryl]-β-alanine ethyl ester in 59% yield, melting point 28° (from hexane).

Provenance & Evidence