Hydrochloric Acid → 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 (1.52 g, 5.0 mmol) in N,N-dimethylformamide (10 mL) was treated with sodium methanethiolate (0.59 g, 7.5 mmol). The reaction mixture was then heated to 100-110° C. for 14 h. At this time, the reaction was poured onto a mixture of ice and a 2N aqueous hydrochloric acid solution (25 mL). This mixture was extracted into ethyl acetate (3×35 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). The organics were 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 w/acetic acid) afforded 3-cyclopentyl-2-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-propionic acid (1.36 g, 83.4%) as a pale yellow oil: EI-HRMS m/e calcd for C16H19F3O2S (M+) 332.1058, found 332.1057.

1. additionAt this time, the reaction was poured onto a mixture of ice
2. extractionThis mixture was extracted into ethyl acetate (3×35 mL) and diethyl ether (1×25 mL)
3. washThe organics were then washed with water (1×50 mL)
4. dry with materialThe organics were dried over magnesium sulfate and sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-06204f6b05ce418caeadb37e4f9cb8ca

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06320050B1