Hydrochloric Acid → 1-[2-(2-Ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylic acid trifluoroacetate

Participants

Reaction Steps

To a solution of methyl 1-[2-(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylate (D20) (25 mg) in isopropanol (2 mL) and water (2 mL) at room temperature was added sodium hydroxide (1.874 mg). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was neutralized with 1 M HCl solution. The solvent was removed in vacuo. The residue was dissolved in THF, and filtered. The filtrate was purified by Mass Directed AutoPrep to give 1-[2-(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylic acid (E7) (10 mg) as a TFA salt (off-white solid). δH (DMSO-d6, 400 MHz): 1.11 (3H, t), 1.34 (6H, d), 2.88 (4H, m), 3.43 (2H, m), 3.62 (1H, m), 4.29 (4H, m), 4.94 (1H, m), 7.39 (1H, t), 7.51 (3H, m), 8.24 (2H, m), 10.08 (1H, br s), 13.13 (1H, br s). δF (DMSO-d6, 376 MHz): −73.4, −61.3. MS (ES): C26H28F3N3O3S requires 519. found 520.2 (M+H+).

Provenance & Evidence