Triethylamine → HCID 15021171, compound

Participants

Reaction Steps

To a suspension of 0.54 g (2.19 mmol) of 3-(6-methoxy-3-quinolyl)alanine in 13.5 mL of ethanol was added dropwise 0.68 mL of thionyl chloride at 0° C. The reaction mixture was refluxed overnight, then was evaporated in vacuo. triturated with benzene and evaporated to dryness in vacuo. The crude product, 3-(6-methoxy-3-quinolyl)alanine ethyl ester dihydrochloride, was combined with 0.93 mL (6.4 mmol) of triethylamine and 14.2 mL of 50% aqueous 1,4-dioxane; to that mixture was added, in one portion, 0.58 g (2.4 mmol) of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The resultant mixture was stirred overnight at room temperature, then was diluted with 15 mL of water and extracted twice with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel, using 5:1 methylene chloride/ethyl acetate as eluent, to give a white solid which was recrystallized from isopropyl ether to afford 0.6 g (73.3 %) of the title compound, melting at about 127° C. and having the structural formula: ##STR116## The identity of the product was confirmed by NMR and IR spectral analyses as well as by elemental analysis.

Provenance & Evidence