Electrochemical process for preparing hydroxylaminoeverninomicin

Chemistry: electrical and wave energy – Processes and products

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204 74, 536 17, C25B 304, C07D32500, C07H 1500

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active

039987086

ABSTRACT:
Hydroxylaminoeverninomicins having antibacterial activity are prepared by electrochemically reducing the corresponding everninomicin having a nitro function or the corresponding nitrosoeverninomicin in an aqueous miscible organic solvent under an inert atmosphere or in an anhydrous aprotic solvent in the presence of carbon dioxide. Additionally, nitrosoeverninomicins, upon electrochemical reduction in an aprotic solvent under an inert atmosphere, are converted to the corresponding hydroxylaminoeverninomicins. Preferred starting compounds are everninomicins B, C and D whereby are obtained hydroxylaminoeverninomicins B, C and D, respectively. Particularly useful is the electrochemical reduction of everninomicin D in anhydrous dimethylformamide in the presence of carbon dioxide to obtain hydroxylaminoeverninomicin D of excellent purity in high yields.

REFERENCES:
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patent: 3361653 (1968-01-01), Miller
patent: 3475300 (1969-10-01), Staal
patent: 3505187 (1970-04-01), Austin et al.
patent: 3901973 (1975-08-01), Harris
patent: 3915956 (1975-10-01), Ganguly et al.
patent: 3920629 (1975-11-01), Garrguly et al.

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