Methyl chloroformate → (E,E)-N-[3-[3-(3-thienyl)phenyl]-2-propenyl]-(N'-ethyl-6,6-dimethyl-2-hepten-4-ynylamino)acetamide

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Reaction Steps

100 mg of (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)glycine hydrochloride was dissolved in 10 ml of methylene chloride, and 34 μl of methyl chloroformate and 0.1 ml of triethylamine were added under ice cooling. The mixture was stirred for 30 minutes, and a methylene chloride solution(5 ml) of 90 mg of (E)-3-[3-(3-thienyl)phenyl]-2-propenylamine was added, then the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration and the solvent was evaporated under reduced pressure. The residue was purified by medium-pressure liquid chromatography [silica gel column, hexane→hexane/ethyl acetate=5/1] to give 24 mg (yield 17%) of the captioned compound as a pale yellow oil.

Provenance & Evidence