Hydrochloric Acid → HCID 71239342, compound

Participants

Reaction Steps

To a flask containing ethyl 3-(4-((3,3-dimethylcyclobutyl)(6-fluoroquinolin-3-ylamino)methyl)benzamido)propanoate (7.4 mg, 0.0420 mmol) was added tetrahydrofuran (0.105 mL), methanol (0.105 mL), and 1 N sodium hydroxide (0.105 mL, 0.105 mmol). The reaction was stirred for 4.5 h at room temperature. The reaction was then diluted with ethyl acetate and water. 1 N hydrochloric acid (0.105 mL) was then added dropwise to bring the pH to 3. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to provide 3-(4-((3,3-dimethylcyclobutyl)(6-fluoroquinolin-3-ylamino)methyl)benzamido)propanoic acid (6.7 mg, 99% yield) as a solid. 1H NMR (400 MHz, CD3OD, 6): 8.46 (d, J=2.7 Hz, 1H), 7.83-7.72 (m, 3H), 7.57-7.50 (m, 2H), 7.17-7.09 (m, 2H), 6.85 (d, J=2.7 Hz, 1H), 4.38 (d, J=9.8 Hz, 1H), 3.62 (t, J=6.9 Hz, 2H), 2.69-2.54 (m, 3H), 2.11 (ddd, J=11.4, 7.7, 4.2 Hz, 1H), 1.77 (ddd, J=11.2, 9.0, 2.6 Hz, 2H), 1.63-1.52 (m, 1H), 1.18 (s, 3H), 1.13 (s, 3H). (M+1): 450.3.

Provenance & Evidence