Hydrochloric Acid → HCID 58732805, compound

Participants

Reaction Steps

To a solution of (±)-trans-ethyl 4-(4-{[4-{[(4-chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-difluorobutanoate (190 mg, 0.32 mmol) in THF (4.4 mL) was added a solution of lithium hydroxide (15.2 mg, 0.63 mmol) in water (2 mL). To the resulting mixture was added methanol (2 mL) and the reaction stirred 18 hours at room temperature. The reaction mixture pH was adjusted to 2 via addition of 1N hydrochloric acid and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield (±)-trans-4-(4-{[4-{[(4-chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-difluorobutanoic acid. 1H-NMR (CDCl3) δ: 0.96 (d, 3H), 1.08 (t, 3H), 1.61-1.74 (m, 1H), 2.34-2.56 (m, 3H), 3.52-3.68 (m, 1H), 3.72-3.88 (m, 2H), 4.00-4.14 (m, 2H), 4.93-5.11 (m, 1H), 6.42-6.51 (m, 1H), 6.65-6.82 (m, 4H), 6.83-6.92 (m, 1H), 7.16-7.29 (m, 2H), 7.37-7.50 (m, 4H). MS m/z: 571 (M+1).

Provenance & Evidence