1,5-Naphthalenedisulfonic acid → HCID 11355034, compound

Participants

Reaction Conditions

Reaction Steps

To a 500-mL round-bottomed flask was added the 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 (16 g, 18.5 mmol) and THF (100 mL) and the resulting mixture was stirred until the compound dissolved (about 10 min). A 1M solution of tetrabutylammonium fluoride (37 μL, 37 mmol) in THF was added and the resulting mixture was stirred at 40° C. under nitrogen for 6 to 7 hours (>98% conversion by HPLC). The mixture was then cooled to 30° C., and a solution of naphthalene-1,5-disulfonic acid (4.26 g, 14.8 mmol, recrystallized from acetonitrile) in methanol (100 mL) was added. The reaction mixture was then stirred at 30° C. for 3 to 4 hours and then at room temperature for 2 hours. The resulting crystalline solid was then collected by filtration, washed with methanol (20 mL) and air dried to give the title compound as an off-white crystalline solid (8 g).

Provenance & Evidence