Dichloromethane → 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

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A solution of 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 (15.2 g, 16.7 mmol) in a DCM solution containing 10% 0.5 M ammonium hydroxide in MeOH (150 mL total solution) was loaded onto silica gel (80 g) in a coarse fritted glass funnel which had been previously wetted with a DCM solution containing 10% 0.5 M ammonium hydroxide in MeOH (200 mL). The silica gel was rinsed with a DCM solution containing 20% 0.5 M ammonium hydroxide in MeOH (1×1000 mL); and then with a DCM solution containing 25% 0.5 M ammonium hydroxide in MeOH (1×1000 mL). The filtrate was concentrated under reduced pressure to give a yellow glassy solid (13.6 g). This material was dissolved in DCM (600 mL) and the resulting solution was filtered through a fritted glass filter and the filter was washed with DCM (3×150 mL). The filtrate was concentrated under reduced pressure and the residue was warmed to 50° C. using an oil bath and held under high vacuum overnight to provide the title compound (12.7 g) (contained about 6 wt. % of DCM).

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