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

Temperature

25 °C

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid methyl ester (2.92 g, 7.72 mmol) in tetrahydrofuran/water (3:1, 88 mL) was treated with lithium hydroxide (647 mg, 15.43 mmol). The reaction was stirred at 25° C. for 3 d. The tetrahydrofuran was then removed in vacuo. The residue was diluted with water (50 mL) and extracted with diethyl ether (25 mL). The aqueous layer was acidified to pH=1 with a 3N aqueous hydrochloric acid solution. The product was extracted into ethyl acetate (3×75 mL) and diethyl ether (1×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (2×100 mL), dried over magnesium sulfate and sodium sulfate, filtered, and concentrated in vacuo to give 3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid (2.37 g, 84.5%) as a pale-yellow semi-solid: EI-HRMS m/e calcd for C16H19F3O4S (M+) 364.0956, found 364.0958.

1. customThe tetrahydrofuran was then removed in vacuo
2. additionThe residue was diluted with water (50 mL)
3. extractionextracted with diethyl ether (25 mL)
4. extractionThe product was extracted into ethyl acetate (3×75 mL) and diethyl ether (1×50 mL)
5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (2×100 mL)
6. dry with materialdried over magnesium sulfate and sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-dade413fd2c54de4a0766b4a8752ba9d

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441184B1