Ethyl Acetate → Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-{[(R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}phenylcarbamoyl)-butyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester Dihydrofluoric Acid Salt

Participants

Reaction Steps

To a stirred solution of biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-{[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]-methyl}phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (3.87 g, 4.28 mmol) in a mixture of DCM (20 mL) and DMF (2.5 mL) was added triethylamine trihydrofluoride (2.1 mL, 13 mmol). The resulting mixture was stirred at room temperature overnight. DCM (68 mL) was added to the reaction mixture and then, with stirring, EtOAc (68 mL) was added dropwise. A light colored precipitate formed resulting in a slurry. The slurry mixture was filtered through a medium porosity fritted glass filter and the filter cake was rinsed with EtOAc (2×10 mL) and then pressed dry on a nitrogen press to give the title compound (3.73 g, 99% yield).

Provenance & Evidence