Sodium Hydroxide → HCID 67483012, compound

Temperature

47.5 °C

A solution of (E)-3-cyclopentyl-2-[3-bromo-4-(methanesulfonyl)-phenyl]-acrylic acid methyl ester (357 mg, 0.92 mmol) in ethanol (6 mL) was treated with a 1N aqueous sodium hydroxide solution (2 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 (1×30 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 (2×20 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 (E)-3-cyclopentyl-2-[3-bromo-4-(methanesulfonyl)-phenyl]-acrylic acid (339 g, 98%) as an amorphous solid: EI-HRMS m/e calcd for C15H17BrO4S (M+) 372.0031, found 372.0028.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customto remove ethanol
3. additionThe residue was diluted with water (10 mL)
4. extractionextracted with diethyl ether (1×30 mL)
5. customto remove any neutral impurities
6. extractionthe resulting acid was extracted into ethyl acetate (2×20 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-237cf0d1a7cb4d7d8f1e9ab68ee28191

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353111B1