Water → HCID 58909942, compound

Participants

Reaction Steps

After dissolving the tert-butyl N-{2-bromo-5-ethoxy-4-[(methylamino)carbonyl]benzyl}-N-{2-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-oxoethyl}carbamate (2.71 g) in propionitrile (11 ml), sodium cyanide (420 mg), copper iodide (163 mg) and tetrakis(triphenylphosphine)palladium (495 mg) were added under a nitrogen atmosphere and the mixture was heated to reflux for one hour. Additional copper iodide (170 mg) and tetrakis(triphenylphosphine)palladium (500 mg) were added and heating to reflux was continued for 4 hours. Ethyl acetate and water were added to the reaction mixture and the resultant mixture was filtered with celite. The filtrate was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and, after filtering off the insoluble portion, was concentrated. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (788 mg) as a white solid.

Provenance & Evidence