Hydrochloric Acid → HCID 23368483, compound

Participants

Reaction Steps

To a solution of 0.61 g of 5-amino-3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 18 ml of methanol are added 1.3 ml of a dioxane solution (2.2N) of hydrogen chloride and 0.49 g of 37% formalin at 20°-25° C., and then, 0.19 g of sodium cyanoborohydride is added at 15°-20° C., after which they are subjected to reaction at the same temperature for 30 minutes. Ethyl acetate and water are added to the reaction mixture and the pH is adjusted to 10 with an aqueous sodium hydroxide solution, after which the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=3:2], to obtain 0.60 g of brown, oily 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-dimethylamino-1,2-benzoisoxazole.

Provenance & Evidence