Sodium Hydroxide → HCID 67287184, compound

Participants

Reaction Steps

To a solution of ethyl 6-chloro-7-(4-(6-(4-(trifluoromethyl)phenyl)pyridazin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (1.83 g, 3.07 mmol) in 40 mL of 3:1 THF/EtOH was added sodium hydroxide (12.3 ml, 12.3 mmol). The reaction was stirred for 3 hours, then concentrated. The crude material was combined with 1M HCl (50 mL) and stirred for 3 hours. The material was resolved via supercritical fluid chromatography employing a CHIRALCEL® OJ-H column (3×15 cm) eluting with 35% ethanol/carbon dioxide at 100 bar, using 3 mL injections and a flow rate of 140 mL/min. Collection of fractions containing peak 2 and removal of volatiles provided Enantiomer 2 of 6-chloro-7-(4-(6-(4-(trifluoromethyl)phenyl)pyridazin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid (0.730 g, 1.29 mmol, 41.9% yield) as a white solid. MS (apci, positive) m/z=569.9.

Provenance & Evidence