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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-[({4-[(4-butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]-2-fluorobenzoate (207 mg; 0.38 mmol) in anhydrous THF (7 mL) were added lithium hydroxide monohydrate (158 mg; 3.77 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 185 mg (91.7%) of the title compound as a brown cream. HPLC, Rt: 5.71 min (purity=98.5%). LC/MS, M−(ESI): 534.3. 1H NMR (MeOD) δ: 7.66 (d, J=8.66 Hz, 2H), 7.58 (d, J=8.66 Hz, 3H), 7.46 (d, J=7.91 Hz, 2H), 7.31. (m, 1H), 7.23 (m, 3H), 3.61 (m, 3H), 2.66 (t, J=7.53 Hz, 2H), 1.63 (qt, J=7.34 Hz, 2H), 1.35 (m, 12H), 0.96 (t, J=7.91 Hz, 3H), 0.87 (t, J=6.97 Hz, 3H).

Provenance & Evidence