Ethyl Acetate → AG-G-78469

Participants

Reaction Conditions

Reaction Steps

4.1 g (0.016 mol) of {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4R,5S)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)-methanol from the aforementioned Experimental Example 2 were dissolved in a mixed solvent of 1.0 L dichloromethane and 25 mL pyridine. After cooling the mixture to 0° C., 18 mL (0.236 mol) of methanesulfonyl chloride were added and the resulting solution was stirred for 5 h at 0° C. Saturated sodium bicarbonate solution was added and the compound was extracted with chloroform. The extract was dried, filtered, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using the eluant hexane:ethyl acetate=2:1 to obtain 6.4 g (yield: 98%) of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester as an oil.

Provenance & Evidence