Ammonium formate → 2-[3-{[3-({2-[(tert-Butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

Participants

Reaction Steps

Ammonium formate (425 mg, 6.74 mmol) and 10% palladium on charcoal (200 mg) was added to a solution of benzyl 2-[3-{[3-({2-[(tert-butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 106) (392 mg, 0.67 mmol) in acetonitrile (10 ml), and the reaction stirred at room temperature overnight. The reaction mixture was filtered through Whatman® fibre, and the filtrate concentrated under reduced pressure. The residue was suspended in dichloromethane, basified using I N NaOH solution, and re-acidified to pH 4, using 1N hydrochloric acid. This solution was extracted with ethyl acetate (3×), and the combined organic extracts dried over MgSO4 and evaporated under reduced pressure to give the title compound as a white foam, (180 mg, 58%).

Provenance & Evidence