Sodium Hydroxide → (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-3-nitro-phenyl)-acrylic acid

Temperature

47.5 °C

A solution of (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-3-nitro-phenyl)-acrylic acid methyl ester (597 mg, 1.62 mmol) in ethanol (10 mL) was treated with a 1N aqueous sodium hydroxide solution (8 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 (20 mL) and extracted with diethyl ether (1×50 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 (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-3-nitro-phenyl)-acrylic acid (0.514 g, 90%) as a white solid: mp 244-247° C.; EI-HRMS m/e calcd for C16H19NO6S (M+) 353.0933, found 353.0929.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customto remove ethanol
3. additionThe residue was diluted with water (20 mL)
4. extractionextracted with diethyl ether (1×50 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 (1×100 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-e587006932604f46b7a360992d6ec370

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353111B1