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Generated: September 22, 2017

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Title: Reductive alkylation of glycopeptide antibiotics
Abstract:This invention is concerned with improved processes for reductive alkylation of glycopeptide antibiotics. The improvement residing in providing a source of copper which results in the initial production of a copper complex of the glycopeptide antibiotic. Reductive alkylation of this complex favors regioselective alkylation and increased yields. Copper complexes of the glycopeptide antibiotic starting materials and of the alkylated products are also part of the invention.
Inventor(s): Berglund; Richard Alan (Lafayette, IN), Lockwood; Nancy Anne (Mountlake Terrace, WA), Magadanz; Howard Eugene (Lafayette, ID), Zheng; Hua (Lafayette, ID)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:09/290,204
Patent Claims: 1. An N.sup.4 alkylated glycopeptide antibiotic prepared by the steps of (i) reacting a soluble copper complex of a glycopeptide antibiotic having an amine-containing saccharide at N.sup.4 with a ketone or aldehyde in the presence of a reducing agent selected from the group consisting of sodium cyanoborohydride and pyridine.borane complex to form a copper complex of said alkylated glycopeptide antibiotic; (ii) isolating said copper complex of said N.sup.4 alkylated glycopeptide antibiotic; and (iii) freeing said N.sup.4 alkylated glycopeptide antibiotic by aqueous treatment at a pH.ltoreq.4.

2. The antibiotic of claim 1 wherein said antibiotic is prepared in methanol.

3. The antibiotic of claim 1 wherein said aldehyde or ketone is present in a slight excess.

4. The antibiotic of claim 1 wherein said reducing agent is present in at least an equimolar amount.

5. The antibiotic of claim 1 wherein said soluble copper complex in step (i) is a 1:1 copper complex with A82846B.

6. The antibiotic of claim 5 wherein said aldehyde is 4'-chloro-4-biphenylcarboxaldehyde.

7. The antibiotic of claim 1 wherein said antibiotic is prepared at a pH between 6 and 8.

8. The antibiotic of claim 7 wherein said pH is between 6.3 and 7.0.

9. The antibiotic of claim 1 wherein said soluble copper complex in step (i) is prepared by adding a source of soluble copper to a glycopeptide antibiotic having an amine-containing saccharide at N.sup.4.

10. The antibiotic of claim 9 wherein said source of soluble copper is copper (II) acetate.

11. A copper-antibiotic complex consisting essentially of copper and with a reductively alkylated glycopeptide antibiotic prepared by reacting a soluble copper complex of a glycopeptide antibiotic having an amine-containing saccharide at N.sup.4 with a ketone or aldehyde in the presence of a reducing agent selected from the group consisting of sodium cyanoborohydride and pyridine.borane.

12. The copper-antibiotic complex of claim 11 wherein said aldehyde is 4'-chloro-4-biphenylcarboxaldehyde.

13. The copper-antibiotic complex of claim 11 wherein said glycopeptide antibiotic having an amine-containing saccharide at N.sup.4 is selected from the group consisting of A82846A, A82846B, A82846C and orienticin A.

14. The copper-antibiotic complex of claim 13 wherein said glycopeptide antibiotic having an amine-containing saccharide at N.sup.4 is A82846B.

15. The copper-antibiotic complex of claim 14 wherein said aldehyde is 4'-chloro-4-biphenylcarboxaldehyde.
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