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Synthesis method of AT-TBA

A ceftazidime side-chain acid and a synthesis method technology, applied in the field of ceftazime side-chain acid synthesis, can solve the problems of restricting the development of ceftazime drug, complex synthesis process, difficult to control, etc., and achieve easy control of conditions, high yield and simple process Effect

Inactive Publication Date: 2012-06-27
太仓市运通化工厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ceftazidime side-chain acid is one of the important intermediates of semi-synthetic ceftazime medicine, its quality and yield directly affect the quality of the synthetic drug ceftazime and the level of cost, in the prior art, due to the synthesis of ceftazime side-chain acid The process is complicated and difficult to control, which limits the development of ceftazidime drug

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Add 35.6g (0.1mol) of ethyl ceftazidime side chain acid, 334mL of methanol, 166mL of water and 6.4g (0.16mol) of NaOH in sequence to a 1L four-neck flask equipped with a condenser tube and mechanical stirring. The reaction was stirred for 8h. Track the reaction with TLC. After the reaction is over, add 2 g of activated carbon and stir for 1 h, filter, cool the filtrate to below 20 °C, adjust the pH to 7 with 1 mol / L hydrochloric acid, and recover methanol by distillation under reduced pressure at 40-45 °C. Dissolve the filtrate in 75mL of water, adjust the pH value to 3 with 1mol / L hydrochloric acid, cool down to 5°C, continue to stir for 30min, filter with suction, wash the filter cake with 50mL of water and 50mL of acetonitrile in turn, and dry the filter cake in vacuum to obtain a light yellow solid 28.3g, which is ceftazidime side chain acid, and the yield is 86%.

Embodiment 2

[0014] Add 71.2g (0.2mol) of ethyl ceftazidime side chain acid, 712mL of methanol, 284mL of water and 8g (0.2mol) of NaOH into a 2L four-necked flask equipped with a condenser and mechanical stirring, and stir at 45-50°C Reaction 10h. Use TLC to track the reaction. After the completion, add 2 g of activated carbon and stir for 2 h, filter, cool the filtrate to below 20 ° C, adjust the pH to 7 with 1 mol / L hydrochloric acid, and recover methanol under reduced pressure at 40 ~ 45 ° C. Dissolve the filtrate in 60mL of water, adjust the pH value to 3 with 1mol / L hydrochloric acid, cool down to 5°C, continue to stir for 1h, filter with suction, wash the filter cake with 50mL of water and 50mL of acetonitrile in turn, and dry the filter cake in vacuum to obtain a light yellow solid 55.5g, namely ceftazidime side chain acid, the yield is 84%.

Embodiment 3

[0016] Add 17.8g (0.05mol) of ethyl ceftazidime side chain acid, 143mL of methanol, 35.6mL of water and 4g (0.1mol) of NaOH in sequence to a 500mL four-neck flask equipped with a condenser and mechanical stirring. The reaction was stirred for 9h. Use TLC to track the reaction, after the end, add 2g of activated carbon and stir for 1.5h, filter, cool the filtrate to below 20°C, adjust the pH to 7 with 1mol / L hydrochloric acid, and recover methanol by distillation under reduced pressure at 40-45°C. Dissolve the remaining filtrate in 90mL of water, adjust the pH value to 3 with 1mol / L hydrochloric acid, cool down to 5°C, continue to stir for 45min, filter with suction, wash the filter cake with 50mL of water and 50mL of acetonitrile in turn, and dry the filter cake in vacuum to obtain light yellow 14.4 g of the solid was ceftazidime side-chain acid, and the yield was 82%.

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Abstract

The invention discloses a synthesis method of AT-TBA, which comprises the following steps: sequentially BPTA, methanol, water and NaOH into a reaction vessel, stirring to react at 45-50 DEG C for 8-10 hours, adding activated carbon, stirring for 1-2 hours, filtering, cooling the filtrate to below 20 DEG C, regulating the pH value to 7, distilling under reduced pressure at 40-45 DEG C to recycle the methanol, dissolving the residual filtrate in water, regulating the pH value to 3, cooling to 5 DEG C, continuing stirring for 0.5-1 hour, carrying out vacuum filtration, sequentially washing the filter cake with water and acetonitrile, and carrying out vacuum drying on the filter cake to obtain a light yellow solid which is the AT-TBA. The synthesis method disclosed by the invention has the advantages of simple technique, easily controlled conditions and high yield, and can implement industrial production.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of ceftazidime side chain acid. Background technique [0002] Ceftazidime belongs to the third-generation cephalosporin antibiotics and was discovered in 1978. In 1983, it was first developed and marketed by the British Glaxo Company. In 1992, ceftazidime was listed for the first time in my country, and in 1993 it was officially included in the list of essential medicines in my country. After more than 10 years of clinical application verification, ceftazidime has the characteristics of broad antibacterial spectrum and enzyme resistance, and it has strong antibacterial activity against Pseudomonas aeruginosa. Ceftazidime side-chain acid is one of the important intermediates of semi-synthetic ceftazime medicine, its quality and yield directly affect the quality of the synthetic drug ceftazime and the level of cost, in the prior art, due ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40
Inventor 张卫东
Owner 太仓市运通化工厂
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