Process for the preparation of amikacin precursors

Details Process for the preparation of amikacin precursors Process for the preparation of amikacin precursors

1995-06-02

1997-04-15

Peselev, Elli

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 137, 536 185, C07H 100

Patent

active

056210850

ABSTRACT:
Process for the preparation of a 3,6'-di-N-Acyl-1-[L-(-)-4-Acylamino-2-hydroxybutyryl] kanamycin A, wherein Acyl is a N-protecting acylating group, which comprises reacting kanamycin A with an aluminum salt in an inert organic solvent, treating the aluminum complex thus obtained with a N-acylating agent and acidifiying the reaction mixture, as such or after having removed the complexing aluminum in basic medium and isolated the 3,6'-di-N-Acyl-kanamycin A, to pH 6, treating the protonated 3,6'-di-N-Acyl-kanamycin A, in form of a salt thereof, with an active derivative of L-(-)-4-Acyl-amino-2-hydroxybutyric acid, wherein Acyl is a N-protecting group preferably identical with that which protects the amino groups in the positions 3 and 6' of kanamycin A, and isolating the product thus obtained by simple correction of the pH.

REFERENCES:
patent: 4140849 (1979-02-01), Umezawa et al.
patent: 4902790 (1990-02-01), Mangia et al.
patent: 4985549 (1991-01-01), Giobbio et al.
Tsuchiya et al., 1-N-Acylation of Aminocyclitol Antibiotics Via Zinc Chelation and Regiospecific N-Trifluoroacetylation, Tetrahedron Letters No. 51, pp. 4951-4954.
N.M. Alykov, Complex Compounds of Pyrocatechol Volet with Aluminum and Aminogloycoside Antibiotics, Astrakhan Pedagogical Institute, vol. 39, No. 8, pp. 1425-1427, 1984.

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