Hydrochloric Acid → 4-({{4-[(4-Butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amino}-methyl)benzoic acid

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To a solution of methyl 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)-ethyl]amino}methyl)benzoate (980 mg, 1.78 mmol) in MeOH (15 mL) was added an aqueous solution of NaOH (4.5 mL, 1N) and the resulting mixture was stirred at rt for 12 hrs. An aqueous solution of HCl (1N) was added and the resulting mixture was extracted with Et2O. The combined organic layers were dried over MgSO4 and evaporated to give 929 mg of 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amino}-methyl)benzoic acid as a colorless oil. This product was dissolved in Et2O (30 mL) and a solution of HCl in dioxane (2 mL, 4N) was added. The precipitate was filtered, washed with Et2O and dried under vacuum to give 985 mg (97%) of the title compound as a white powder. HPLC, Rt: 4.7 min (purity: 98.9%). M−(ESI): 534.3; M+(ESI): 536,2. 1H NMR (DMSO-d6) δ: 13.4 (brs, 1M), 11.3 (brs, 1H), 8.35-7.28 (m, 16H), 4.82-4.45 (m, 2H), 3.96-4.58 (m, 6H), 2.81 (t, J=7.9 Hz, 2H), 1.84-1.68 (m, 2H), 1.60-1.41 (m, 2H), 1.10 (t, J=7.2 Hz, 3H).

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