Water → Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl ester

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Reaction Steps

A solution of 12.1 g of (3R,5S)-5-[(R)-2-benzyloxy-1-hydroxyethyl]-3-propyldihydrofuran-2-one obtained in Example (116c) (43.5 mmol) in methylene chloride (300 ml) was cooled in an ice bath. Then, 13.2 g of triethylamine (131 mmol) and 7.30 g of methanesulfonyl chloride (63.7 mmol) were added thereto, and the mixture was stirred at the same temperature for one hour. 500 ml of water was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=4/1-1/1) to obtain 15.2 g of the title compound (yield: quant.).

Provenance & Evidence