4-Cyanobenzoic acid → N-[(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]-4-cyanobenzamide

Participants

Reaction Steps

1.44 g (3.01 mmol) of t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate was dissolved in 5 ml of 4 N dioxane hydrochloride and 2.5 ml of dioxane, and the solution was stirred for 15 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in 10 ml of dichloromethane. 488 mg (3.3 mmol) of 4-cyanobenzoic acid 1.3 ml (9.3 mmol) of triethylamine, 633 mg (1.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 445 mg (3.3 mmol) of 1-hydroxybenzotriazole were added to the solution, and they were stirred for 16 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by the silica gel column chromatography to obtain the title compound.

Provenance & Evidence