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

Participants

Reaction Steps

A solution of 7.80 g of (3R,5S)-5-[(R)-2-benzyloxy-1-hydroxyethyl]-3-methyldihydrofuran-2-one obtained in Example (76c) (31.2 mmol) in methylene chloride (200 ml) was cooled in an ice bath. Then, 9.45 g of triethylamine (93.6 mmol) and 5.36 g of methanesulfonyl chloride (47.0 mmol) were added thereto, and the mixture was stirred at the same temperature for three hours. 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 9.90 g of the title compound (yield: 97%).

Provenance & Evidence