To a flask containing ethyl 3-(4-((3,3-dimethylcyclobutyl)(7-fluoroquinolin-3-ylamino)methyl)benzamido)propanoate (6.20 mg, 0.0130 mmol) was added tetrahydrofuran (0.0330 mL), methanol (0.0330 mL), and 1 N sodium hydroxide (0.0330 mL, 0.0330 mmol). The reaction was stirred for 18 h at room temperature. The reaction was then diluted with ethyl acetate and water. 1 N hydrochloric acid (0.0330 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)(7-fluoroquinolin-3-ylamino)methyl)benzamido)propanoic acid (3.5 mg, 60% yield) as a solid. 1H NMR (400 MHz, CD3OD, 6): 8.53 (d, J=2.7 Hz, 1H), 8.45 (t, J=5.7 Hz, 1H), 7.80-7.72 (m, 2H), 7.59-7.51 (m, 3H), 7.43 (dd, J=10.0, 2.6 Hz, 1H), 7.23 (td, J=8.8, 2.5 Hz, 1H), 6.99 (d, J=2.5 Hz, 1H), 4.38 (d, J=9.6 Hz, 1H), 3.67-3.57 (m, 2H), 2.67-2.60 (m, 3H), 2.16-2.06 (m, 1H), 1.78 (d, J=2.5 Hz, 2H), 1.63-1.52 (m, 1H), 1.18 (s, 3H), 1.13 (s, 3H). (M+1): 450.3.
