Tributylphosphine → 3-(4-{1-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentyloxy}-benzoylamino)-propionic acid methyl ester

Participants

Reaction Steps

A solution of 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (232 mg, 1.04 mmol) and 1-[4-(5-trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-ol (258 mg, 0.830 mmol) in toluene (5.0 mL) is degassed and filled with nitrogen for 3 times. Tributyl-phosphine (0.310 mL, 1.50 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (316 mg, 1.50 mmol). The reaction mixture is allowed to warm to room temperature and stirred over night, the mixture is loaded on silica gel column. The 3-(4-{1-[4-(5-trifluoromethyl-pyridin-2-yl)-phenyl]-pentyloxy}-benzoylamino)-propionic acid methyl ester (205 mg, 0.40 mmol), 47%, is obtained in purified form after flash column chromatography.

Provenance & Evidence