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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-{[({4-[(4-butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]methyl}-2-fluorobenzoate (66 mg; 0.12 mmol) in THF (4 mL) were added lithium hydroxide monohydrate (49 mg; 1.17 mmol) and water (1 mL). The reaction mixture was stirred at 100° C. for 2500 s under MW. The mixture was poured into HCl 1N (10 mL) and extracted with EtOAc (2×75 mL). Combined organic layers were washed with brine (125 mL), dried over magnesium sulfate and filtrated. The solvent was removed under reduced pressure to give 57 mg (88.6%) of the title compound as a white powder. HPLC: Rt=5.71 min (purity=98.9%), LC/MS: M−(ESI): 548.3.1H NMR (MeOD) δ: 7.87 (d, J=8.6 Hz, 3H), 7.72 (d, J=8.6 Hz, 2H), 7.69 (m, 1H), 7.48 (d, J=7.9 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 7.18 (s, 1H), 4.39 (s, 2H), 3.75 (m, 1H), 3.55 (t, J=4.3 Hz, 1H), 3.16 (t, J=7.3 Hz, 2H), 2.68 (t, J=7.7 Hz, 2H), 1.63 (q, J=7.5 Hz, 3H), 1.35 (m, 4H), 1.15 (m, 4H), 0.95 (t, J=7.3 Hz, 3H), 0.82 (t, J=7.0 Hz, 3H).

Provenance & Evidence