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

Temperature

47.5 °C

A solution of 3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester (1.00 g, 3.08 mmol) in ethanol (15 mL) was treated with a 1N aqueous sodium hydroxide solution (6 mL). The solution was heated at 45-50° C. for 15 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-phenyl)-propionic acid (570 mg, 60%) as a white solid: mp 139-143° C.; EI-HRMS m/e calcd for C16H22O4S (M+) 310.1239, found 310.1241.

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-6f2125683f2d4bcfb7fe040561bb1471

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610846B1