[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]2[CH2:17][CH:16]3[CH:14]([CH2:15]3)[CH2:13][CH:12]2[C:18]([O-:20])=[O:19])=[CH:5][CH:4]=1.CO.[OH-].[Li+]>COCCOC>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]2[CH2:17][CH:16]3[CH:14]([CH2:15]3)[CH2:13][CH:12]2[C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1Methyl(1S/R,3R/S,4R/S,6R/S)-4-({[4-(methylsulfanyl)phenyl]-sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylate was dissolved in ethylene glycol dimethyl ether (3.0 mL) and methanol (1 mL) in a 25 mL round bottom flask. Aqueous solution of lithium hydroxide (3.0 mL, 6.0 mmol, 2 M) was added and the reaction mixture was stirred at ambient temperature for 36 h. After acidification with 2 M aqueous hydrochloric acid to pH 3, the product was extracted into ether. The combined ether extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to give (1S/R,3R/S,4R/S,6R/S)-4-({[4-(methylsulfanyl)phenyl]sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylic acid.
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