Hydrochloric Acid → [2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethylamino]-acetic acid hydrochloride salt

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Reaction Steps

To a stirring solution of [2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethylamino]-acetic acid methyl ester (70 mg, 0.11 mmol) in THF (10 ml) and water (3.3 ml) was added lithium hydroxide monohydrate (12 mg, 0.28 mmol). The resulting mixture was stirred at room temperature for 18 hours and acidified with HCl (0.5 ml, 1 M in water). The crude mixture was concentrated in vacuo and then extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried over sodium sulfate, filtered and concentrated in vacuo. Preparative HPLC (YMC 75×30 mm, 25 ml/min, 25-100% CH3CN) afforded the title compound as the free base. The diamine was treated with 1 M HCl in Et2O (0.11 ml, 0.11 mmol), and the Et2O was evaporated to afford the title compound as an off-white solid, 31 mg (45%). MS(ES) m/e 625.4 (M+).

Provenance & Evidence