Diethyl Ether → 2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorobenzoic acid

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Reaction Steps

To a solution of (2R, 5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoic acid methyl ester (4.12 g, 9.18 mmol) in tetrahydrofuran (10 ml), methanol (10 ml) and water (4 ml) was added lithium hydroxide monohydrate (1.93 g, 45.9 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction was then concentrated, diluted with 1N hydrochloric acid and extracted with dichloromethane (2×). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to give a white foam. Triteration in dichloromethane and diethyl ether gave the title compound (1.38 g, 35% yield).

Provenance & Evidence