Acetic Acid → HCID 44546893, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound 7 (42.5 g, 140 mmol) in 48% HBr (200 mL) was added AcOH (100 mL) to give a light yellow suspension. The reaction was heated to give a light yellow solution and stirred at 120° C. for 6 hr (<1.5% starting material left by HPLC), then concentrated. Dichloromethane (500 mL) was added to the residue and the suspension was filtered. The filtrate was neutralized with ice water, 50% NaOH (added slowly) and Na2CO3 solution to pH of 10. The aqueous layer was extracted with dichloromethane twice. The solid was fully dissolved in dichloromethane and triethylamine (25 mL), and washed with Na2CO3 solution to pH of 10. The organic layers were combined and washed with NaHCO3 and brine, dried over Na2SO4 overnight, filtered and concentrated. The crude product Compound 8, as the free base, can be used in the next step without further purification.

Provenance & Evidence