Water → methyl 5-acetamido-4-amino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Participants

Reaction Steps

To a reaction vessel, 55 g of methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate, 500 ml of denatured alcohol and 100 ml of water was added under stirring at room temperature. To the reaction mass 14 g ammonium chloride and 18 g zinc dust was added. The reaction mixture was stirred at 20° C.-30° C. for 30 minutes. On completion of reaction, the reaction mass was cooled to 10° C. and then filtered through hyflo. The filtrate was concentrated under vacuum to obtain a solid product which was then dissolved in about 200 ml of methylene dichloride. The organic layer was filtered and concentrated to yield 52 g of solid title compound, dried under vacuum (yield—94%, HPLC purity—96%).

Provenance & Evidence