Ethanol → HCID 58732735, compound

Participants

Reaction Steps

(±)-trans-4-(4-{4-[(4-Chloro-phenyl)-ethyl-carbamoyl]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester (520 mg, 0.923 mmol) was dissolved in tetrahydrofuran (15 mL). A solution of lithium hydroxide (77 mg, 1.8 mmol) in water (5 mL) was added. Ethanol was added until the reaction was homogeneous. The resulting solution was allowed to stir at room temperature overnight. The solution was concentrated to remove ethanol and tetrahydrofuran. The resulting aqueous mixture was acidified with concentrated hydrochloric acid until pH=1-2. The heterogeneous mixture was immediately extracted with ethyl acetate (2×75 mL). The extracts were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was a mixture of cis and trans isomers. A portion of the crude residue was purified by HPLC to afford pure (±)-trans-4-(4-{4-[(4-chloro-phenyl)-ethyl-carbamoyl]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid and pure (±)-cis-4-(4-{4-[(4-chloro-phenyl)-ethyl-carbamoyl]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid. The remainder of the mixture was used without further purification in subsequent reactions. Data for the trans isomer: 1H-NMR (CD3OD) δ: 0.97 (d, 3H), 1.12 (t, 3H), 4.73 (ddd, 1H), 2.00-2.13 (m, 2H), 2.47-2.58 (m, 3H), 3.61-3.99 (m, 5H), 5.02-5.12 (m, 1H), 6.44 (d, 1H), 6.68-6.74 (m, 2H), 6.75-6.83 (m, 2H), 6.85-6.92 (m, 1H), 7.17-7.25 (m, 3H), 7.42-7.51 (m, 4H). MS m/z: 535 (M+1).

Provenance & Evidence