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Method for preparing meropenem

A technology of preparation steps and main raw materials, applied in the field of organic synthesis and preparative chemistry, can solve the problems of low yield, unsuitable for large-scale production, low-temperature storage, etc., and achieve the effects of stable process, cost saving of raw materials, and mild conditions

Inactive Publication Date: 2012-03-14
ASYMCHEM LAB TIANJIN +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method purifies the product by non-radioactive TLC method, the yield is low, and the product exists in the form of solution, which needs to be stored at low temperature and is not suitable for large-scale production

Method used

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  • Method for preparing meropenem
  • Method for preparing meropenem
  • Method for preparing meropenem

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Embodiment 1: A method for preparing meropenem, characterized in that the specific preparation steps are as follows:

[0037] Add 20 kg (5 vol) of N-methylmorpholine and acetic acid buffer solution with pH = 6.8 into a 100L reactor, cool down to 0±2°C, add 2 kg (0.5 g / g) of 10% platinum carbon, 2-methyl Add 17.8kg of the main raw material (4kg, 1eq) solution diluted with tetrahydrofuran (4vol) dropwise to 7.6kg of oxalic acid (8eq) solution diluted with 2-methyltetrahydrofuran (1vol), and keep warm at 0±2°C for 5h until the reaction is complete. After the reaction is complete, filter with suction, extract the filtrate twice with 15kg (5vol*2) of methyl tert-butyl ether, add 200g (0.05g / g) of activated carbon to the water phase for decolorization, filter, and add 320kg (100vol) of acetone dropwise to the water phase Crystallization, the crude product of meropenem was dissolved and separated by membrane to obtain 1.43 kg of meropenem, with a yield of 65% and a purity of 9...

Embodiment 2

[0038] Embodiment 2: A method for preparing meropenem, characterized in that the specific preparation steps are as follows:

[0039]Add 20 kg (10 vol) of N-methylmorpholine and acetic acid buffer solution of pH = 7.5 into the 100 L reaction kettle, cool to 10 ± 2 ℃, add 1.2 kg (0.6 g / g) of 10% palladium carbon successively, tetrahydrofuran (8 vol ) diluted main raw material (2kg, 1eq) solution 16.2kg, add dropwise 5.1kg of formic acid (12eq) solution diluted with tetrahydrofuran (2vol), and keep warm at 10±2°C for 4.5h until the reaction is complete. After the reaction is completed, filter with suction, extract the filtrate twice with 11kg (6vol*2) of tetrahydrofuran, add 160g (0.08g / g) of activated carbon to the water phase for decolorization, filter, and crystallize by adding 237kg (150vol) of acetonitrile dropwise to the water phase to obtain the 880g of meropenem was obtained by membrane separation after the crude product was dissolved, with a yield of 80% and a purity of ...

Embodiment 3

[0040] Embodiment 3: A method for preparing meropenem, characterized in that the specific preparation steps are as follows:

[0041] Add 4.8kg (15vol) of N-methylmorpholine and acetic acid buffer solution at pH = 7.8 to a 20L reactor, and add 320g (1g / g) of Raney nickel and methyl tert-butyl ether in sequence at 15±2°C (10vol) diluted main raw material (320g, 1eq) solution 2.7kg, add dropwise 1.7kg of glyoxylic acid (15eq) solution diluted with methyl tert-butyl ether (5vol), and keep warm at 15±2°C for 4.5h to The response is complete. After the reaction is complete, filter with suction, extract the filtrate twice with 2.8kg (10vol*2) of 2-methyltetrahydrofuran, add 32g (0.1g / g) of activated carbon to the water phase for decolorization, filter, and add 57kg (200vol) of tetrahydrofuran dropwise to the water phase Crystallization, the crude product of meropenem was obtained. After the crude product was dissolved, it was separated by membrane to obtain 132 g of meropenem, with ...

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Abstract

The invention relates to a method for preparing meropenem. The method comprises the following step of: reducing beta-methyl carbapenem protected by a meropenem precursor into meropenem under the transferring and catalyzing actions of hydrogen. The method has the advantages of mild chemical reaction conditions, stable process conditions, easiness for operating, high transformation rate, high yield, product purity stabilized over 99 percent, recycling of solvents and catalysts in the entire process, and great saving in the production cost, and is a practicably synthesizing process suitable for large-scale production; and a novel thought and a novel method for a penem compound are provided.

Description

(1) Technical field: [0001] The invention relates to the field of organic synthesis and preparative chemistry, in particular to a method for preparing meropenem. (two) background technology: [0002] So far, there have been a large number of natural or synthetic β-lactamase inhibitors reported, which can be divided into oxypenems, penems, carbapenems, monocyclic β-lactam oxypenems from the chemical structure Among them, carbapenems, especially β-methyl carbapenems, have good antibacterial effects on many drug-resistant bacteria, especially have a strong inhibitory effect on β-type enzymes, and are a series of unique inhibitors. Inhibitor of β-lactamase. [0003] Meropenem (structure as formula I) is a new type of semi-synthetic carbapenem antibiotic for parenteral administration after imipenem-cilastatin developed by Sumitomo Corporation, and it is also the first application The clinical 1β-methyl carbapenem antibiotics have good chemical stability and are stable to β-lact...

Claims

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Application Information

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IPC IPC(8): C07D477/20C07D477/06
Inventor 洪浩陈朝勇周炎李常峰
Owner ASYMCHEM LAB TIANJIN
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