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Method for preparing oritavancin

A biphenyl and raw material technology, applied in the field of oritavancin preparation, can solve the problems of cumbersome reaction operation and post-treatment, etc., and achieve the effects of increased yield, easy reaction operation, and simple post-treatment

Active Publication Date: 2016-12-07
BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reductive alkylation of this complex is beneficial to regioselective alkylation and increased yield, the reaction operation and post-treatment are cumbersome, and what is directly obtained is the copper complex of oritavancin, and it is necessary to add oritavancin Star released from copper complex

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] N 2 Under protection, Brettpho catalyst (10.1mg, 1.26×10 -2 mmol), Brettphos ligand (6.77mg, 1.26×10 -2 mmol), 4-(bromomethyl)-4'-biphenyl chloride (0.142g, 0.504mmol), A82846B acetate (1.0g, 0.605mmol), potassium tert-butoxide (0.27g, 2.42mmol) and 1 , 4-dioxane 10ml. The reaction mixture was heated to 100°C and kept for 8 hours. After the reaction was completed, the reaction solution was filtered to remove insoluble matter, and the obtained filtrate was purified by Preparative HPLC. The preparation solution was desalted and concentrated in vacuo to remove the organic solvent, and freeze-dried to obtain 0.769 g of the final product oritavancin, with a yield of 70.88%.

Embodiment 2

[0021] N 2 Under protection, Brettphos catalyst (10.1mg, 1.26×10 -2 mmol), Brettphos ligand (6.77mg, 1.26×10 -2 mmol), 4-(chloromethyl)-4'-biphenyl chloride (0.120g, 0.504mmol), A82846B acetate (1.0g, 0.605mmol), potassium tert-butoxide (0.27g, 2.42mmol) and toluene 10ml. The reaction mixture was heated to 100°C and kept for 10 hours. After the reaction was completed, the reaction solution was filtered to remove insoluble matter, and the obtained filtrate was purified by Preparative HPLC. The preparation solution was desalted and concentrated in vacuo to remove the organic solvent, and freeze-dried to obtain 0.725 g of the final product oritavancin, with a yield of 66.82%.

Embodiment 3

[0023] N 2 Under protection, Brettphos catalyst (10.1mg, 1.26×10 -2 mmol), Brettphos ligand (6.77mg, 1.26×10 -2 mmol), 4-(bromomethyl)-4'-biphenyl chloride (0.142g, 0.504mmol), A82846B acetate (1.0g, 0.605mmol), sodium tert-butoxide (0.23g, 2.42mmol) and 1 , 4-dioxane 10ml. The reaction mixture was heated to 100°C and kept for 8.5 hours. After the reaction was completed, the reaction solution was filtered to remove insoluble matter, and the obtained filtrate was purified by Preparative HPLC. The preparation solution was desalted and concentrated in vacuo to remove the organic solvent, and freeze-dried to obtain 0.756 g of the final product oritavancin, with a yield of 69.68%.

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Abstract

The invention discloses an improved method for preparing oritavancin. The method takes A82846B acetate as a raw material, under existence of a Brettphos catalyst, a Brettphos ligand, alkali and a solvent, the material and an amino alkylation reagent are subjected to a reaction to generate oritavancin with one step. According to the invention, reaction steps are simplified, the selectivity of amino alkylation is increased, oritavancin yield is increased, and a route suitable for large industrial production is provided.

Description

technical field [0001] The invention relates to an improved preparation method of oritavancin. In particular, the present invention relates to the regioselective amine alkylation of A82846B. Background technique [0002] Glycopeptide antibiotics are a large class of substances produced by microorganisms, or produced and partially modified by microorganisms. Vancomycin and teicoplanin are commercially available antibacterial products. Among the glycopeptides discovered in the 1990s are those known as A82846A (also known as ereomomycin), A82846B (also known as chloroorienticinA), A82846C (also known as orienticinC) and orienticin A . A variety of modifications have been made to naturally occurring glycopeptides, one of which is the reductive alkylation of reactive amines in glycopeptides. The A82846B structure is as follows: [0003] . [0004] Oritavancin is a novel semi-synthetic glycopeptide antibiotic developed by Eli Lilly. It was launched in the United States on...

Claims

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Application Information

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IPC IPC(8): C07K9/00
Inventor 袁建栋黄仰青池建文
Owner BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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