Sodium Hydroxide → (E)-3-cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-acrylic acid

Temperature

47.5 °C

A solution of (E)-3-cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-acrylic acid methyl ester (199 mg, 0.52 mmol) in ethanol (3 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-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-acrylic acid (172 mg, 90%) as a yellow paste: EI-HRMS m/e calcd for C17H17F3N4O2 (M+) 366.1309, found 366.1309.

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-f87eba866dbc49009372b69ddd53ad8e

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369232B1