Potassium Hydroxide → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

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Reaction Conditions

Reaction Steps

The mixture of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester and 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid ethyl ester, from above, (937 mg) was dissolved in ethanol (30 mL) and allowed to dissolve. To this solution was then added a solution of potassium hydroxide (733 mg, 13.1 mmol) in water (7 mL). The yellow solution was then stirred for 3 h at 25° C. It was concentrated in vacuo to remove the ethanol and then IN hydrochloric acid was added until the pH=2. This was then extracted with methylene chloride (3×15 mL). The organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate plus 1% acetic acid) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (787 mg, 82% over two steps) as a white solid: mp: 123.9-126.2° C.; FAB-HRMS m/e calcd for C15H19O4SCl (M+H)+331.0771, found 331.0776.

Provenance & Evidence