Novel process for the synthesis of amikacin
AssigneePierrel S.p.A.
InventorsAlberto Mangia, Vicenzo Giobbio, Giorgio Ornato
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Abstract
A novel process for the synthesis of amikacin starting from kanamycin A protected at the positions 3 and 6' is described comprising the reaction of kanamycin A with a salt of a bivalent metal cation selected from zinc, nickel, iron, cobalt, manganese, copper and cadmium in the presence of water as the solvent or co-solvent followed by the in situ reaction of the resulting complex with a reactive derivative of L-amino-2-hydroxy-butyric acid, removal of the metal cation of the protecting groups and purification of the thus obtained raw product. The acylation under these conditions is extremely selective.
Claims18
A process for the selective synthesis of amikacin from kanamycin A protected in the 3- and 6' positions, said process comprising the steps of:
- reacting kanamycin A protected in the 3- and 6'-positions with a salt of a bivalent metal cation selected from the group consisting of zinc, nickel, iron, cobalt, manganese, copper, cadmium and mixtures thereof in the presence of an effective amount of water as a solvent or co-solvent to form a complex;
- reacting said complex with a derivative of L-(-)-4-amino-2-hydroxybutyric acid wherein the amino group is protected and the carboxyl group is activated;
- and
- destroying the complex by removing the metal cation and removing the protective groups.
Dependencies are inferred from the claim text.