Acetic Acid → (3-{(r)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((s)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic acid hydrochloride salt

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Reaction Steps

A solution of compound (3-{(R)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic acid methyl ester (50 mg, 0.1 mmol) in THF (9 ml) and water (6 ml) was treated with aqueous LiOH (1.0 N, 1.0 ml, 1.0 mmol). After stirring at room temperature for 2 h, additional LiOH (1.0 ml, 1.0 mmol) was added and stirring was continued for 2 h. The reaction was neutralized with AcOH and poured into water and ethyl acetate. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, v detection at 254 nm) to give the free acid of title compound as an oil (40 mg, 75%). MS m/e 534.2 (M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M) to precipitate the HCl salt. The suspension was filtered and dried to give the title compound as a white solid.

Provenance & Evidence