Sodium Hydroxide → HCID 67165334, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-trans-methyl 5-(4-{[4-{[(4-chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (500 mg, 0.87 mmol) in 1:1 THF/methanol (5.0 mL) was added a solution of sodium hydroxide (69.5 mg, 1.74 mmol) in water (1.0 mL). The resulting mixture was heated at 60° C. for 18-20 hours and concentrated. The resulting residue was dissolved in water (˜50 mL), cooled to 0° C., and the solution acidified using 3N hydrochloric acid. The resulting precipitated material was collected via suction filtration, washed with 1N hydrochloric acid (3×25 mL), and dried to afford crude 5-(4-{[4-{[(4-Chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoic acid as a mixture of cis and trans isomers. Purification via HPLC yielded (±)-trans-5-(4-{[4-{[(4-Chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoic acid (23%).

Provenance & Evidence