Potassium Hydroxide → HCID 21958970, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid methyl ester (prepared as in Example 8, 75 mg, 0.23 mmol) in ethanol (5 mL) was treated with a solution of potassium hydroxide (32 mg, 0.58 mmol) in water (1 mL). The reaction was stirred for 3 h at 25° C. The reaction was then concentrated in vacuo to remove the ethanol and then acidified to pH=2 with a 1N aqueous hydrochloric acid solution. This solution was then extracted with methylene chloride 3×15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, hexanes to 60/40 hexanes/ethyl acetate plus 1% acetic acid) afforded 2-(4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid (60 mg, 85%) as a white solid: FAB-HRMS m/e calcd for C15H20O5S (M+H)+ 313.1109. found 313.1111.

Provenance & Evidence