Sodium Azide → (2R, 3R, 4S, 4aS, 10aR)-2-azidomethyl-8-chloro-3, 4-diacetoxy-10-(2-diethylaminoethyl)-2, 3, 4, 4a, 10, 10a-hexahydropyrano [3, 2-b] [1, 4] benzothiazine

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Reaction Conditions

Reaction Steps

To the solution of 14.0 g of the compound (36) obtained in Example 35 in 140 ml of dimethylsulfoxide, 14.0 g of sodium azide was added, and the mixture was heated with stirring for 45 minutes at 100 ° C. The reaction solution was poured into ice water, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 10.1 g (yield 90.2%) of the title compound from the fraction of chloroform-acetone (1:1).

Provenance & Evidence