Sodium methanethiolate → 3-Cyclopentyl-2-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-propionic acid

Temperature

105 °C

A solution of 3-cyclopentyl-2-(4-fluoro-3-trifluoromethyl-phenyl)-propionic acid (prepared in Example 87, 1.52 g, 5.0 mmol) in N,N-dimethylformamide (10 mL) was treated with sodium methanethiolate (593 mg, 7.5 mmol). The reaction mixture was then heated to 100-110° C. for 14 h. At this time, the reaction was cooled to 25° C. and poured onto a IN aqueous hydrochloric acid solution (25 mL) and extracted into ethyl acetate (3×25 mL) and diethyl ether (1×25 mL). The organics were then washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (3×75 mL), dried over magnesium sulfate and sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-propionic acid (1.37 g, 82.4%) as a pale yellow oil: EI-HRMS m/e calcd for C16H19F3O2S (M+) 332.1058, found 332.1057.

1. temperatureAt this time, the reaction was cooled to 25° C.
2. extractionextracted into ethyl acetate (3×25 mL) and diethyl ether (1×25 mL)
3. washThe organics were then washed with water (1×50 mL)
4. dry with materiala saturated aqueous sodium chloride solution (3×75 mL), dried over magnesium sulfate and sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-ca2806740e794b7ab6fde82d41f3de46

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06320050B1