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Deprotection method in meropenem synthesis

A technology of meropenem and deprotection group, applied in the field of deprotection group in the synthesis of meropenem, can solve the problems of low weight yield, high equipment and operation requirements, and achieve the effects of high yield, low equipment investment and simple operation

Inactive Publication Date: 2012-02-01
HUBEI YITAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The catalytic hydrogenation reaction must be carried out under high pressure, which requires high equipment and operation, and the preparation and reaction time is more than 7 hours, and the weight yield is less than 50%.

Method used

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  • Deprotection method in meropenem synthesis
  • Deprotection method in meropenem synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 500ml four-neck flask, add 175ml of tetrahydrofuran, slowly add 11g of protected meropenem while stirring, dissolve until clear, add 150g of pure water and 5g of ammonium formate while stirring;

[0020] Slowly raise the temperature to reflux, stir and reflux for 30 minutes, cool to normal temperature, add measured 1.5g of palladium catalyst and 5g of pure water and mix evenly into the flask, wash with a small amount of water and put into the flask. Slowly warming up to reflux again, reflux reaction for 2 hours;

[0021] Cool to normal temperature, vacuum filter, wash the filter cake with hot water at 90°C, and drain it. Filtrate is transferred in the 2000ml three-neck flask;

[0022] Quickly add 500g of acetonitrile into the three-necked flask, and cool down to 10--15°C. Within 10-15 minutes, 600g of acetonitrile was added dropwise under rapid stirring, and the temperature was controlled at 10--15°C. Stir to grow crystals for 1 hour. Suction filtration, the fi...

Embodiment 2

[0024] In a 1000ml four-neck flask, add 350ml of methanol, slowly add 22g of protected meropenem under stirring, dissolve until clear, add 300g of pure water and 8g of formic acid under stirring;

[0025] Slowly heat up to reflux, stir and reflux for 30 minutes, cool to normal temperature, add metered 4g of 10% palladium carbon catalyst and 10g of pure water and mix evenly into the flask, wash with a small amount of water and put into the flask. Slowly warming up to reflux again, reflux reaction for 2 hours;

[0026] Cool to normal temperature, vacuum filter, wash the filter cake with hot water at 90°C, and drain it. Filtrate is transferred in the 5000ml three-neck flask;

[0027] Quickly add 1000g of acetone to the three-necked flask, and cool down to 10--15°C. Within 10-15 minutes, add 1200g of acetone dropwise under rapid stirring, and control the temperature at 10--15°C. Stir to grow crystals for 1 hour. Suction filtration, the filter cake was rinsed with 50g of aceton...

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Abstract

A deprotection method in meropenem synthesis comprises the following steps of: removing p-nitrobenzyl and p-nitrobenzyl oxygen formyl from meropenem in an organic solvent 1 or a hydrous organic solvent 1 (such as an alcohol or ether or ester compound under the action of a catalyst and a reducing agent, filtering, and adding an organic solvent 2 (such as acetonitrile or acetone) to precipitate meropenem. The method provided by the invention can be carried out at normal pressure, has advantages of low equipment investment, simple operation, mild reaction, good selectivity, high yield and the like, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a process or method for deprotecting groups in the synthesis of meropenem. Background technique [0002] Penem drugs are new antibiotics with a new chemical structure developed by American medical researchers in the 1970s. It belongs to β-lactam antibiotics like penicillins and cephalosporins. Clinical studies have shown that penems have strong antibacterial activity against Gram-positive and negative bacteria, and can also be used to deal with infections caused by various common methicillin-resistant strains. According to the latest report from the international antibiotic industry, among the three fastest-growing new antibiotic drugs in the international pharmaceutical market in the past few years, penems are at the top of the list. [0003] Protecting meropenem from p-nitrobenzyl and p-nitrobenzyloxyformyl is one of the necessary steps in the production of meropenem products....

Claims

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Application Information

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IPC IPC(8): C07D477/20C07D477/08
Inventor 王正友严建华胡绪炳杨博
Owner HUBEI YITAI PHARMA
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