Chemical synthesis of 6-O-alkyl erythromycin A
AssigneeAbbott Laboratories
InventorHemantkumar H. Patel
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Abstract
A process of preparing 6-O-alkyl erythromycin A is provided. The process includes the steps of protecting the oxime hydroxyl of 9-oxime erythromycin A with a benzoyl protecting group, protecting the 2'-hydroxyl group and optionally the 4'-hydroxyl group with an O-protecting group, alkylating the 6-hydroxyl, removing the benzoyl and O-protecting groups and deoximating the 9-oxime.
Claims14
A process of preparing 6-O-methyl erythromycin A comprising the steps of:
- a) benzoylating 9-oxime erythromycin A to form a 9-oximebenzoyl erythromycin A derivative;
- b) protecting the 2'-hydroxyl group of the 9-oximebenzoyl erythromycin A derivative to form a 2' protected -9-oximebenzoyl erythromycin A derivative;
- c) methylating the 2',-protected-9-oximebenzoyl erythromycin A derivative to form a 2',-protected-6-O-methyl-9-oximebenzoyl erythromycin A derivative;
- d) removing the benzoyl and O-protecting groups from the 2'-protected -6-O-methyl-9-oximebenzoyl erythromycin A derivative to form 6-O-methyl-9-oxime erythromycin A;
- and
- e) deoximating the 6-O-methyl-9-oxime erythromycin A to form 6-O-methyl erythromycin A.
A compound of the structure (I), ##STR6## wherein R.sup.5 is disubstituted benzene, R.sup.6 is hydrogen or alkyl and R.sup.7 and R.sup.8 are each independently hydrogen, trimethylsilyl or an O-protecting group.
Dependencies are inferred from the claim text.