Methanol → HCID 57595424, compound

Participants

Reaction Steps

3-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}benzoic acid was prepared following general procedure H, substituting methyl 3-(chlorocarbonyl)benzoate for 6-trifluoromethyl nicotinyl chloride. (Methyl 3-(chlorocarbonyl)benzoate was prepared in one step from 3-(methoxycarbonyl)benzoic acid. Treatment of this carboxylic acid with oxalyl chloride and catalytic DMF afforded methyl 3-(chlorocarbonyl)benzoate in decent yield). Hydrolysis of methyl 3-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}benzoate with lithium hydroxide, water, methanol and tetrahydrofuran yielded 3-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}benzoic acid.

Provenance & Evidence