Lithium Hydroxide → 3-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester (865 mg, 2.43 mmol) in tetrahydrofuran (6 mL) was treated with a 0.8M aqueous lithium hydroxide solution (4.6 mL, 3.65 mmol). The reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was concentrated in vacuo to remove tetrahydrofuran. The resulting aqueous residue was diluted with water (25 mL) and then treated with a 1N aqueous hydrochloric acid solution (10 mL). The resulting aqueous layer was then extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/4 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid (723 mg, 87%) as a white foam. Analytical data indicated the presence of a small impurity; however, the 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid was used without further purification in subsequent reactions.

Provenance & Evidence