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Cefazolin acetoxy analogue preparation method

A technology for cefazolin acetoxy analogs, which is applied in the field of preparation of cefazolin acetoxy analogs, can solve problems such as undiscovered, and achieve the effects of easy separation and purification, and simple and quick synthesis operations

Inactive Publication Date: 2019-02-01
河北合佳医药科技集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no literature report on the preparation of this impurity by means of chemical synthesis in China.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 20.05g of 7-ACA and 150mL of dichloromethane into a 500mL four-neck flask, stir for 15min, control the temperature to -5°C~-10°C, add 9.8mL of tetramethylguanidine dropwise, and the dropwise addition is completed in about 15min, and continue to stir for 30min until the 7-ACA is completely dissolved, cool down to -30°C for later use; add 150mL of dichloromethane, 23.52g of tetrazoleacetic acid, 40.2mL of N,N-dimethylacetamide into another 500mL four-necked bottle, and control the temperature at -10 ℃~-15℃, stir for 15min, add 10mL triethylamine dropwise in about 20min, stir for 15min after adding, add 10mL pivaloyl chloride dropwise in about 30min, stir for 2h; Add dropwise into tetrazolium acetic acid mixed anhydride, stir for 1 hour, then control the temperature at 10-35°C, add 200mL of water, adjust the pH to 6.0-6.5 with triethylamine, stir and hydrolyze for 15 minutes, collect the water phase, decolorize with activated carbon, and filter , add 10% hydrochloric a...

Embodiment 2

[0032] Add 20.03g of 7-ACA and 150mL of dichloroethane into a 500mL four-neck flask, stir for 15 minutes, control the temperature to -10°C to -25°C, add 10.1mL of tetramethylguanidine dropwise, and continue stirring after about 15 minutes. 30min until 7-ACA is completely dissolved, cool down to -30°C for later use; add 150mL dichloroethane, 23.69g tetrazoleacetic acid, 41.5mL N,N-dimethylacetamide to another 500mL four-necked bottle, and control the temperature -20℃~-35℃, stir for 15min, add 10mL triethylamine dropwise in about 20min, stir for 15min after the addition, add 10mL pivaloyl chloride dropwise in about 30min, stir for 2h; control temperature <-30℃, add 7-ACA Add the dissolved solution dropwise to tetrazole acetic acid mixed anhydride, stir and react for 1h, then control the temperature at 10-35°C, add 200mL of water, adjust the pH to 7.0-7.5 with triethylamine, stir and hydrolyze for 15min, collect the water phase, and decolorize it with activated carbon , filter, a...

Embodiment 3

[0034]Add 20.12g of 7-ACA and 150mL of toluene into a 500mL four-neck flask, stir for 15min, control the temperature to -25°C~-35°C, add 12.4mL of tetramethylguanidine dropwise, and finish adding in about 15min, continue stirring for 30min until Dissolve all 7-ACA, cool down to -30°C for later use; add 150mL toluene, 23.16g tetrazolium acetic acid, 40.8mL N,N-dimethylacetamide to another 500mL four-necked bottle, and control the temperature at -35°C to -40°C ℃, stir for 15min, add 10mL triethylamine dropwise for about 20min, stir for 15min after adding, add 10mL pivaloyl chloride dropwise for about 30min, stir for 2h; In azole acetic acid mixed anhydride, stir and react for 1h, then control the temperature at 10-35°C, add 200mL of water, adjust the pH to 8.0-8.5 with triethylamine, stir and hydrolyze for 15min, collect the water phase, decolorize with activated carbon, filter, add 10% Adjust the pH to 1.5-2.5 with hydrochloric acid, then reduce the temperature of the system to...

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Abstract

The invention discloses a cefazolin acetoxy analogue preparation method, wherein the cefazolin acetoxy analogue finished product is prepared by using a 7-ACA solution and a tetrazoleacetic acid mixedanhydride solution as reaction raw materials and carrying out matched control on the raw material ratio, the reaction temperature and the pH value of the system. According to the present invention, the process method for preparing the cefazolin acetoxy analogue by using the chemical synthesis method is provided, such that the cefazolin acetoxy analogue standard substance can be stably and efficiently obtained so as to improve the production quality of cefazolin sodium.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation process of cefazolin acetoxy analogs. Background technique [0002] Cefazolin sodium, the chemical name is (6R,7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-7-[(1H- Sodium tetrazol-1-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate. Cefazolin sodium is the first-generation cephalosporin with a broad antibacterial spectrum. It is suitable for the treatment of otitis media, bronchitis, pneumonia and other respiratory tract infections, urinary tract infections, skin and soft tissue infections, bone and joint infections, sepsis, and infectious diseases caused by sensitive bacteria. Endocarditis, hepatobiliary system infection and eye, ear, nose, throat and other infections; it can also be used as a preventive drug before surgery. [0003] During the production of cefazolin sodium, the raw material 7-ACA reacts with tetrazoleacetic acid to g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/06C07D501/12
CPCC07D501/06C07D501/12C07D501/34
Inventor 刘振强孟龙超刘东娜梁丙辰刘新元曹晓倩王宇栋白伟东
Owner 河北合佳医药科技集团股份有限公司
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