Method for the synthesis of desferrioxamine B and analogs thereo

Details Method for the synthesis of desferrioxamine B and analogs thereo Method for the synthesis of desferrioxamine B and analogs thereo

1989-05-17

1991-01-22

Brust, Joseph Paul

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

Organic compounds

Hydroxamic acids, chalcogen analogs or salts thereof

558390, 558391, 558394, 558446, 558451, 558452, 560312, 564153, C07C25906

Patent

active

049872532

ABSTRACT:
Disclosed is a synthesis of desferrioxamine B and analogs and homologs thereof beginning with the generation of the O-protected N-(4-cyanobutyl)hydroxylamine which is acylated at the O-benzylhydroxylamine nitrogen with either succinic or acetic anhydride. The resulting half-acid amide or amide respectively, is subjected to a series of high yield condensations and reductions which provide desferrioxamine B in 45% overall yield. Finally, a desamino analog of desferrioxamine is prepared in order to demonstrate the synthetic utility of the scheme as applied to desferrioxamine derivatives.

REFERENCES:
patent: 3118823 (1964-01-01), Gaeumann et al.
patent: 3153621 (1984-10-01), Gaeumann et al.
Greene, "Protective Groups in Organic Synthesis", pp. 9-15, 50 and 72, [Date unknown], John Wiley & Sons, N.Y., Chichester, Brisbane, Toronto, Singapore.

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