Biphenyl-2-ylcarbamic Acid 1-(9-{Benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethyl]amino}nonyl)-piperidin-4-yl Ester → HCID 66967735, compound

Participants

Reaction Steps

To a 500-mL round-bottomed flask was added a sample of the crude solution of biphenyl-2-yl-carbamic acid 1-(9-{benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydro-quinolin-5-yl)-2-(tert-butyldimethyl-silanyloxy)ethyl]amino}nonyl)piperidin-4-yl ester (50 mL containing about 17.5 g, 18.5 mmol) and methanol (150 mL) and the resulting mixture was stirred until homogeneous (if necessary, any undissolved solids can be removed by filtration through a pad of Celite). The flask was then purged with hydrogen gas for 5 minutes and then palladium hydroxide (3.5 g, 20% Pd (dry basis) on carbon, 60% water) was added. The resulting mixture was stirred at room temperature while hydrogen gas was slowly bubbled through the mixture for about 5 hours (>98% conversion by HPLC). The reaction mixture was then filtered through a pad of Celite and the solvent was removed under reduced pressure to give crude biphenyl-2-yl-carbamic acid 1-{9-[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}piperidin-4-yl ester as a yellow solid (16 g).

Provenance & Evidence