Hydrochloric Acid → 5-[{4-[(4-Butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoate (170 mg; 0.33 mmol) in THF (7 mL) were added lithium hydroxide monohydrate (139 mg; 3.31 mmol) and water (3 mL). The reaction mixture was stirred under MW at 100° C. for 2500 s. Then an aqueous solution of HCl (1N) was added and the mixture extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and the solvent was removed under reduced pressure to give 147 mg (88.9%) of the title compound as a colorless solid. HPLC, Rt: 5.54 min (purity=98.4%), LC/MS: M−(ESI): 498.3. 1H NMR (MeOD) δ: 7.61 (m, 1H), 7.29 (d, J=7.9 Hz, 5H), 7.22 (d, J=7.9 Hz, 2H), 7.08 (d, J=7.9 Hz, 2H), 7.03 (s, 1H), 3.8 (m, 2H), 2.52 (t, J=7.5 Hz, 2H), 1.49 (q, J=7.4 Hz, 4H), 1.25 (m, 8H), 0.82 (m, 6H).

Provenance & Evidence