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3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid methyl ester

lithium hydroxide

→

3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid

수율 84.5%

용매

tetrahydrofuran water

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후처리

1. 1
   기타The tetrahydrofuran was then removed in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water (50 mL)
3. 3
   추출extracted with diethyl ether (25 mL)
4. 4
   추출The product was extracted into ethyl acetate (3×75 mL) and diethyl ether (1×50 mL)
5. 5
   세척The combined organic layers were washed with a saturated aqueous sodium chloride solution (2×100 mL)
6. 6
   건조dried over magnesium sulfate and sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid methyl ester (2.92 g, 7.72 mmol) in tetrahydrofuran/water (3:1, 88 mL) was treated with lithium hydroxide (647 mg, 15.43 mmol). The reaction was stirred at 25° C. for 3 d. The tetrahydrofuran was then removed in vacuo. The residue was diluted with water (50 mL) and extracted with diethyl ether (25 mL). The aqueous layer was acidified to pH=1 with a 3N aqueous hydrochloric acid solution. The product was extracted into ethyl acetate (3×75 mL) and diethyl ether (1×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (2×100 mL), dried over magnesium sulfate and sodium sulfate, filtered, and concentrated in vacuo to give 3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid (2.37 g, 84.5%) as a pale-yellow semi-solid: EI-HRMS m/e calcd for C16H19F3O4S (M+) 364.0956, found 364.0958.

출처