Hydrochloric Acid → HCID 54263751, compound

Participants

Reaction Steps

To a solution of 16 mg of 2-methylthio-4-hydroxy-5-(6-methoxycarbonylhexylidene)-4-octyl-2-cyclopentenone obtained in Example 101, dissolved in 1 ml of acetone, 11 ml of 0.1M phosphate buffer of pH 8 was added. Under stirring, 1.5 mg of pig liver esterase was added, and the mixture was stirred at 30-35° C. for 130 hours. After the mixture was adjusted to pH 4 with 0.1N hydrochloric acid, ammonium sulfate was added to saturation and the mixture was filtered with addition of ethyl acetate. The filtrate was extracted with ethyl acetate, the organic layers were combined and washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, filtration and concentration, the concentrate was subjected to silica gel column chromatography to give 7.7 mg (yield 47%) of 2-methylthio-5-(6-carboxyhexylidene)-4-hydroxy-4-octyl-2-cyclopentenone.

Provenance & Evidence