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A kind of preparation method of cefazolin lactone

A technology of cefazolin and lactone, which is applied in the field of preparation of cefazolin lactone, can solve problems such as undiscovered, and achieve the effects of easy separation and purification, and simple and fast synthesis operation.

Active Publication Date: 2020-05-26
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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  • A kind of preparation method of cefazolin lactone
  • A kind of preparation method of cefazolin lactone

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Add 15.75g of D-7-ACA and 150mL of dichloromethane into a 500mL four-neck flask, stir for 15 minutes, control the temperature at -5°C to -15°C, add 10.2mL of tetramethylguanidine dropwise, the dropwise addition is completed in about 15 minutes, continue Stir for 30 minutes until D-7-ACA is completely dissolved, cool down to -30°C, and set aside; add 150mL of dichloromethane, 24.74g of tetrazoleacetic acid, 41.3mL of N,N-dimethyl Acetamide, temperature control -10℃~-25℃, stirring for 15min, adding 11mL triethylamine dropwise in about 20min, stirring for another 15min, adding 12mL pivaloyl chloride dropwise in about 30min, stirring for 2h; temperature control at -30℃ Next, add the D-7-ACA solution dropwise into tetrazole acetic acid mixed anhydride, stir for 1 hour, then control the temperature at 10-35°C, add 200 mL of water, adjust the pH to 7.0-7.5 with triethylamine, stir and hydrolyze for 15 minutes , collect the water phase, decolorize with activated carbon, filter,...

Embodiment 2

[0032] Add 15.82g of D-7-ACA and 150mL of dichloromethane into a 500mL four-necked flask, stir for 15 minutes, control the temperature to -15°C to -35°C, add 10.4mL of tetramethylguanidine dropwise, and the dropwise addition is completed in about 15 minutes. Continue to stir for 30 minutes until D-7-ACA is completely dissolved, cool down to -30°C, and set aside; add 150mL of dichloromethane, 25.23g of tetrazoleacetic acid, 41.6mL of N,N-dimethyl Acetamide, temperature control -25℃~-40℃, stirring for 15min, adding 11mL triethylamine dropwise for about 20min, stirring for another 15min, adding 12mL pivaloyl chloride dropwise for about 30min, stirring for 2h; temperature control at -30 Below ℃, add the D-7-ACA solution dropwise into tetrazole acetic acid mixed anhydride, stir for 1 hour, then control the temperature at 10-35℃, add 200mL of water, adjust the pH to 8.0-8.5 with saturated sodium carbonate solution, and stir Hydrolyze for 15 minutes, collect the water phase, decolori...

Embodiment 3

[0034]Add 7.88g of D-7-ACA and 100mL of dichloromethane into a 500mL four-neck flask, stir for 10min, control the temperature to -15°C ~ -35°C, add 5.2mL of tetramethylguanidine dropwise, and the dropwise addition is completed in about 15min. Continue to stir for 30 minutes until D-7-ACA is completely dissolved, cool down to -30°C, and set aside; add 100mL dichloromethane, 12.38g tetrazoleacetic acid, 20.73mL N,N-dimethyl Acetamide, temperature control -10℃~-35℃, stir for 10min, add 5.5mL triethylamine dropwise for about 10min, stir for another 10min, add 6mL pivaloyl chloride dropwise for about 15min, stir for 1h; control temperature at - Below 30°C, add D-7-ACA solution dropwise into tetrazolium acetic acid mixed anhydride, stir for 30 minutes, then control the temperature at 10-35°C, add 100mL of water, adjust the pH to 9.0-9.5 with triethylamine, and stir Hydrolyze for 15 minutes, collect the water phase, decolorize with activated carbon, filter, add 10% hydrochloric acid ...

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Abstract

The invention discloses a preparation method of cefazolin lactone, which comprises D-7-ACA (7-amino-3-hydroxyl-3-cephalosporin-4-carboxylic acid) solution and tetrazoleacetic acid mixed anhydride The solution is the reaction raw material, and the finished product of cefazolin lactone is obtained through a series of operations of adding water for extraction, temperature control, acid-base control, filtration and washing. The invention provides a process method for preparing cefazolin lactone by means of chemical synthesis, which can stably and efficiently obtain a standard product of cefazolin lactone, thereby improving 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 lactone. 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 process of cefazolin sodium, the cefazolin acetoxy analogue undergoes a self-cycling reac...

Claims

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Application Information

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