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Synthesis method of carbapenem antibiotic parent nucleus MAP

A technology for carbapenems and a synthesis method, which is applied in the field of pharmaceutical intermediates, can solve the problems of inability to meet the requirements of environmental protection, many three wastes, etc., and achieves the effects of less harsh reaction conditions, low price, and reduced energy consumption and cost.

Inactive Publication Date: 2015-11-18
SUZHOU KAKEA BIOCHEM SCI & TECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The MAP synthesis method in the prior art has many three wastes, which can no longer meet the requirements for environmental protection

Method used

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  • Synthesis method of carbapenem antibiotic parent nucleus MAP

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of synthetic method of carbapenem antibiotic mother nucleus MAP is characterized in that, comprises the following steps:

[0026] 1) Add p-nitrobenzyl malonate, dichloromethane, and anhydrous magnesium chloride into a nitrogen-protected reaction vessel, and add triethylamine dropwise at room temperature, and react for 3 hours to obtain anhydrous magnesium salt;

[0027] 2) Add 4-MBA, dichloromethane, CDI and anhydrous magnesium salt into a nitrogen-protected reaction vessel, keep it warm at 30°C for 7-8 hours, add hydrochloric acid after cooling down to 25°C, stir for 30 minutes, let stand to separate and separate Separate the organic layer to obtain the organic solution of intermediate A;

[0028] 3) Add toluenesulfonyl azide to the organic solution of intermediate A, raise the temperature to 50°C for 2 hours, concentrate at 40°C to obtain a brown oil, then add isopropanol to the brown oil, and cool down to Crystallization at 5-10°C, and solid-liquid separation...

Embodiment 2

[0036] A kind of synthetic method of carbapenem antibiotic mother nucleus MAP is characterized in that, comprises the following steps:

[0037] 1) Add p-nitrobenzyl malonate, dichloromethane, and anhydrous magnesium chloride into a nitrogen-protected reaction vessel, and add triethylamine dropwise at room temperature, and react for 2 hours to obtain anhydrous magnesium salt;

[0038] 2) Add 4-MBA, dichloromethane, CDI and anhydrous magnesium salt into a nitrogen-protected reaction vessel, keep warm at 20°C for 7h, add hydrochloric acid after cooling down to 20°C, stir for 20min, let stand to separate layers and separate the organic Layer obtains the organic solution of intermediate A;

[0039] 3) Add toluenesulfonyl azide to the organic solution of intermediate A, raise the temperature to 50°C for 1 hour, concentrate at 40°C to obtain a brown oil, then add isopropanol to the brown oil, cool down to Crystallization was carried out at 5°C, and intermediate B was obtained by sol...

Embodiment 3

[0047] A kind of synthetic method of carbapenem antibiotic mother nucleus MAP is characterized in that, comprises the following steps:

[0048]1) Add p-nitrobenzyl malonate, dichloromethane, and anhydrous magnesium chloride into a nitrogen-protected reaction vessel, and add triethylamine dropwise at room temperature, and react for 3 hours to obtain anhydrous magnesium salt;

[0049] 2) Add 4-MBA, dichloromethane, CDI and anhydrous magnesium salt into a nitrogen-protected reaction vessel, keep warm at 30°C for 8h, add hydrochloric acid after cooling down to 30°C, stir for 30min, let stand to separate layers and separate the organic Layer obtains the organic solution of intermediate A;

[0050] 3) Add toluenesulfonyl azide to the organic solution of intermediate A, heat up to 50°C for 2 hours, concentrate at 45°C to obtain a brownish-yellow oil, then add isopropanol to the brownish-yellow oil, cool down to Crystallization was carried out at 10°C, and intermediate B was obtained...

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Abstract

The invention discloses a synthesis method of carbapenem antibiotic parent nucleus MAP. Compared with the prior art, the method redesigns an MAP synthesis route, enhances the synthesis efficiency, has the advantages of lower reaction raw material price, low reaction conditions and lower three wastes, lowers the energy consumption and cost, and satisfies the environment-friendly requirement.

Description

technical field [0001] The invention belongs to the field of pharmaceutical intermediates, in particular to a method for synthesizing carbapenem antibiotic mother nucleus MAP. Background technique [0002] Carbapenem antibiotics are a new class of β-lactam antibiotics that were developed and explored in the 1970s. This type of drug has the advantages of strong antibacterial activity, wide antibacterial spectrum, very stable to β-lactamase, and low toxicity. Based on these rare qualities, it is now a clinical treatment for bacterial mixed infections, especially severe It is a very effective antimicrobial drug for severe bacterial infection after surgery, and has occupied an irreplaceable important position in the global antibiotic market. [0003] In 1976, researchers from Merck in the United States extracted thiamycin from the fermentation broth of Streptomyces streptomyces in livestock, which was the first carbapenem antibiotic in history, and found that it was effective a...

Claims

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Application Information

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IPC IPC(8): C07F9/6561
Inventor 张广明蔡建萍张李锋陈曾飞
Owner SUZHOU KAKEA BIOCHEM SCI & TECH LTD
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