Ozone → N-benzyloxycarbonyl-N-(2-oxo-ethyl)-D-alanine t-butyl ester

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Reaction Steps

Cbz-N-allyl-D-alanine t-butylester (70) in methylene chloride is treated with ozone at -78° C. until a blue color persists. The ozonide is quenched with dimethylsulfide and allowed to warm to room temperature. Excess dimethylsulfide is removed by bubbling a stream of nitrogen into the solution. After evaporation of solvent the product is purified by flash chromatography over silica gel to give (71).

Provenance & Evidence