Tetrahydrofuran → HCID 58636785, compound

Participants

Reaction Steps

To a solution of sodium hydride (124 mg, 60% in oil, 3.1 mmol) in anhydrous tetrahydrofuran (10 mL) was added methyl diethyl phosphonoacetate (661 mg, 3.1 mmol) at −78° C. under nitrogen atmosphere and stirred for 15 minutes. To the reaction mixture was added 5-(3-cyano-benzyloxy)-4-formyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (109) (523 mg, 1.1 mmol) and stirred for 15 minutes. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 1:1) as an eluant to give (E)-3-[5-{[tert-butoxycarbonyl-(4-cyano-phenyl)-amino]-methyl}-3-(3-cyano-benzyloxy)-2-methyl-pyridin-4-yl]-acrylic acid methyl ester (120) (428 mg, 738% yield) as a colorless oil.

Provenance & Evidence