Triethylamine → HCID 178459631, compound

Participants

Reaction Steps

In 5 ml of N,N-dimethylformamide were dissolved 67 mg of bis(2-fluorobenzyl)acetic acid and 100 mg of (2RS, 3S)-3-[N-(L-histidyl)amino]-4-cyclohexyl-2-hydroxybutyric acid isopropyl ester dihydrochloride, and to the solution were successively added 0.06 ml of diphenylphosphoryl azide and 0.1 ml of triethylamine with stirring under ice-cooling. The mixture was still stirred for 16 hours, and the reaction mixture was evaporated under reduced pressure. To the residue was added an aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: chloroform/methanol=10/1) to 23 mg of (2RS, 3S)-3-{N-[bis(2-fluorobenzyl)acetyl]-L-histidyl}amino-4-cyclohexyl-2-hydroxybutyric acid isopropyl ester having an Rf2 value of 0.59 as a white powder.

Provenance & Evidence