Abbott Laboratories Corporation

Alexandra E Graham

Albert V Thomas

David A Riley

Shyamal I Parekh

Michael John Dipierro

Rachel R Yang

A process for the preparation of 4'-deoxyerythromycins, having the formula: ##STR1## wherein R is H or OH, R.sup.1 is H or loweralkyl, and R.sup.2 is H or CH.sub.3 by treatment of the starting material, 2'-O-acetyl-4'-imidazolylthiocarbamoyl-erythromycin, with a hypophosphite reagent, in a water-miscible protic solvent optionally comprising a phase transfer agent. In a preferred embodiment, the water-miscible solvent is an alcohol and the starting material is reacted with sodium hypophosphite, ACVA and tetra-n-butylammonium hydroxide.

Hypophosphite deoxygenation reactions in the synthesis of erythromycin

A process for the preparation of 4'-deoxyerythromycins, having the formula: ##STR1## wherein R is H or OH, and R.sup.1 is H or loweralkyl by treatment of the 2'-O-acetyl-4'-imidazolylthionocarbonyl-erythromycin starting material with the radical initiator 4,4'-azobis-(4-cyanovaleric acid), H.sub.3 PO.sub.2 and an organic base in a water-miscible solvent and optionally eliminating the 2'-O-acetyl group. In a preferred embodiment, the water-miscible solvent is an alcohol and the deoxygenation and deacetylation is carried out in one step.

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Mundelein, IL, United States of America

Alexandra E Graham