Synthesis of 7-halo-7-deoxylincomycins
AssigneeThe Upjohn Company
InventorDouglas A. Livingston
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Abstract
An improved process for preparing 7-halo-7-deoxylincomycins and analogs thereof. The compounds prepared have anti-bacterial activity.
Claims11
A process for preparing a compound selected from the group consisting of 7-halo-7-deoxylincomycin and analogs thereof which comprises (a) reacting a compound selected from the group consisting of lincomycin and analogs thereof with an amide halide having the formula ##STR2## wherein halogen is a bromine or chlorine atom, R.sub.1 and R.sub.2 are the same or different and are selected from the group consisting of aryl, alkyl containing one to eight carbon atoms, inclusive, or when taken together with the nitrogen atom to which they are attached form a heterocyclic ring selected from the group consisting of (a) a heterocyclic ring containing carbon and nitrogen of four to eight ring atoms and (b) morpholino;
- (b) heating the adduct formed in step (a) to form a 7-halo-7-deoxy adduct;
- and
- (c) hydrolyzing the 7-halo-7-deoxy adduct formed in step (b) with an aqueous base;
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- (d) isolating the 7-halo-7-deoxylincomycin compound.
A process for preparing a lincomycin adduct which comprises reacting a compound selected from the group consisting of lincomycin and analogs thereof with an amide halide having the formula ##STR3## wherein halogen a bromine or chlorine atom, R.sub.1 and R.sub.2 are the same or different and are selected from the group consisting of aryl, alkyl containing one to eight carbon atoms, inclusive, or when taken together with the nitrogen atom to which they are attached from a heterocyclic ring selected from the group consisting of (a) a heterocyclic ring containing carbon and nitrogen of four to eight ring atoms and (b) morpholino.
Dependencies are inferred from the claim text.