Methanesulfonyl chloride → HCID 86735301, compound

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Reaction Steps

In this example 0.42 g. of methanesulfonyl chloride is added with rapid stirring to a mixture containing 1.2 g. of (+) 3-[5-(hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane-1,2-diol in 20 ml. of pyridine at -30° C. The mixture is then allowed to warm to room temperature and evaporated to dryness affording a residue of (+) 2-hydroxy-1-methylsulfonyloxy-3-(5(-hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane. The residue is then dissolved in 50 ml. of anhydrous methanol and cooled to 0° C. A mixture containing 1 g. of sodium methoxide in 10 ml. of anhydrous methanol is added and the resulting mixture stirred for 2 minutes and then evaporated to remove methanol. 100 Ml. of ethyl acetate is added and the resulting ethyl acetate mixture washed three times with water, dried over magnesium sulfate, and evaporated affording a residue of (+) 1,2-epoxy-3-[5-(hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane.

Provenance & Evidence