Sodium Hydroxide → 3-Cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid

Temperature

47.5 °C

A solution of 3-cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid methyl ester (265 mg, 0.67 mmol) in ethanol (5 mL) was treated with a 1N aqueous sodium hydroxide solution (1.5 mL). The solution was heated at 45-50° C. for 5 h, at which time, thin layer chromatography analysis of the mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to remove ethanol, and the residue was diluted with water (20 mL) and extracted with diethyl ether (1×40 mL) to remove any neutral impurities. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 3-cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid (249 mg, 97%) as a viscous oil: EI-HRMS m/e calcd for C17H21F3O4S (M+) 378.1113, found 378.1121.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. customto remove ethanol
3. additionthe residue was diluted with water (20 mL)
4. extractionextracted with diethyl ether (1×40 mL)
5. customto remove any neutral impurities
6. extractionThe resulting acid was extracted into ethyl acetate (2×50 mL)
7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-ebf825aa7d8e4acd91afc3959a85e5a6

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06320050B1