Dichloromethane → HCID 22388593, compound

Participants

Reaction Steps

(tert-Butoxy)-N-(2-{4-[4-(1-methyl-2-{[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethyl)carboxamide (410 mg, 0.860 mmol, prepared in example 38), trifluoroacetic acid (0.86 mL), and methylene chloride (5.75 mL) were combined and stirred, by stirbar, in a 15 mL round bottom flask, in a nitrogen system, at room temperature, for one hour. The reaction mixture was then concentrated under reduced pressure, and dissolved in excess 5N sodium hydroxide, and extracted three times with 25 mL of methylene chloride. Next the organic extracts were combined, washed with 50 mL of water, dried with potassium carbonate, filtered, and concentrated under reduced vacuum, yielding 480 mg of crude material. This crude material was dissolved in diethyl ether, and anhydrous hydrogen chloride gas was bubbled through the solution, until it was acidic. Next, the acidic solution was allowed to stir, by stirbar, for an additional hour, and then was vacuum filtered, capturing the white precipitate and drying it in a vacuum oven at 40° C. for 30 minutes, yielding the title compound (305 mg, 94%) as a yellow solid.

Provenance & Evidence