Triethylamine → N-[(9H-Xanthen-9-yl)methyl]-N'-{2-t-butyl-5-[4-cyclohexyl-3-(t-butyldimethylsilyloxy)butyl]phenyl}urea

Participants

Reaction Steps

A solution of 240 mg (1.00 mmol) of 2-(9H-xanthen-9-yl)acetic acid, 275 mg (1.00 mmol) of diphenylphosphoryl azide and 139 μl (1.00 mmol) of triethylamine in 3 ml of benzene was heated under reflux, with stirring, for 2.5 hours, after which a solution of 459 mg (1.10 mmol) of 2-t-butyl-5-[4-cyclohexyl-3-(t-butyldimethylsilyl-oxy)butyl]aniline in 0.5 ml of benzene was added. The resulting mixture was heated under reflux for 3 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate, and the diluted mixture was washed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 25 g of silica gel, using a 95:5 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 414 mg (yield 65%) of the title compound as a foam-like material.

Provenance & Evidence