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

A solution of 3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester (95 mg, 0.28 mmol) in ethanol (2 mL) was treated with a 1N aqueous sodium hydroxide solution (1.5 mL). The solution was heated at 45–50° C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was concentrated in vacuo to remove ethanol. The residue was diluted with water (10 mL) and extracted with diethyl ether (1×20 mL) to remove any neutral impurities. The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution, and the resulting acid was extracted into ethyl acetate (2×15 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-cycloheptyl-2-(4-methanesulfonyl-phenyl)-propionic acid (78 mg, 86%) as a white solid: EI-HRMS m/e calcd for C17H24O4S (M+H)+ 325.1474, found 325.1478.

1. temperatureThe solution was heated at 45–50° C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture
2. concentrationThe reaction mixture was concentrated in vacuo
3. customto remove ethanol
4. additionThe residue was diluted with water (10 mL)
5. extractionextracted with diethyl ether (1×20 mL)
6. customto remove any neutral impurities
7. extractionthe resulting acid was extracted into ethyl acetate (2×15 mL)
8. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-8bcf0aa914a44952a32dabc2b461ce80

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223868B2