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The preparation method of 7-amino ceftriaxone

A technology of amino cephalosporin and triazine ring, applied in the field of medicine, can solve the problems of unfavorable sustainable development, increase production cost and high production cost, and achieve the effects of improving competitiveness, improving utilization rate and improving safety

Active Publication Date: 2015-08-19
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method are: the highly volatile, expensive and toxic acetonitrile is used as the solvent, the production cost is high, and the yield is only 90.4%.
The disadvantages of this method are: a raw material (cephalosporin esterase) is introduced, which increases the production cost, and the yield is low at only 85%
[0007] In short, these traditional methods have disadvantages such as high cost of raw materials, most of them are toxic substances, and have a great impact on the environment, which is not conducive to sustainable development.

Method used

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  • The preparation method of 7-amino ceftriaxone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 20g of 7-ACA, 11.7g of triazine ring, 0.12g of EDTA and 0.05g of sodium metabisulfite into a 500mL three-necked flask, stir evenly in 185mL of dimethyl carbonate, and raise the temperature to 24°C. Add 50g BF 3 - Dimethyl carbonate, react at 30°C for 20 minutes. After the reaction was completed, water at 0°C was added, ammonia water was added dropwise until the pH was 2.5 to crystallize, and the crystal was grown at 8°C for 30 minutes, filtered with suction, washed with water, washed with ethanol, and dried to obtain 24 g of dry product. The content detected by high performance liquid chromatography was 99.5%, and the mass yield was 1.20 (based on 7-ACA).

Embodiment 2

[0028] Add 20g of 7-ACA, 12.0g of triazine ring, and 0.08g of EDTA into a 500mL three-necked flask, stir evenly in 100mL of dimethyl carbonate, and raise the temperature to 25°C. Add 36.0g BF 3 - Dimethyl carbonate, react at 15°C for 60 minutes. After the reaction was completed, ethanol at 0°C was added, ammonia water was added dropwise until the pH was 2.9 to crystallize, the crystal was grown at 5°C for 30 minutes, filtered with suction, washed with water, washed with ethanol, and dried to obtain 25.4 g of dry product. The content detected by high performance liquid chromatography was 99.0%, and the mass yield was 1.27 (based on 7-ACA).

Embodiment 3

[0030] Add 20g of 7-ACA, 12.2g of triazine ring, and 0.10g of EDTA into a 500mL three-necked flask, stir evenly in 300mL of dimethyl carbonate, and raise the temperature to 25°C. Add 64.0g BF 3 - Dimethyl carbonate, react at 60°C for 15 minutes. After the reaction was completed, acetone at 0°C was added, and ammonia water was added dropwise until the pH was 3.8 to crystallize. The crystal was grown at 6°C for 25 minutes, filtered with suction, washed with water, and dried to obtain 24.6 g of dry product. The content detected by high performance liquid chromatography was 99.2%, and the mass yield was 1.23 (based on 7-ACA).

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Abstract

The invention belongs to the field of medicines, and specifically relates to a preparation method of 7-amino ceftriaxone sodium. The preparation method comprises the following steps: suspending 7-aminocephalosporanic acid, a triazine ring and EDTA (Ethylene Diamine Tetraacetic Acid) in dimethyl carbonate; adding a boron trifluoride dimethyl carbonate complex; carrying out reaction; performing post-treating to obtain 7-amino ceftriaxone sodium. By adopting 7-aminocephalosporanic acid (ACA) and triazine ring and using an environment-friendly and economical solvent dimethyl carbonate as a solvent and the boron trifluoride dimethyl carbonate complex as a catalyst to synthesize 7-amino ceftriaxone sodium, use of toxic solvents such as volatile acetonitrile is avoided by adopting dimethyl carbonate which has no toxicity, excellent environment-friendly performance and low cost compared with acetonitrile and has the characteristicsof convenience in use, less pollution, easiness in transportation and the like during production as the solvent, so that the reaction process is relatively environment-friendly, and the operating safety is improved. The price of dimethyl carbonate is cheaper than that of acetonitrile, so that the production cost is greatly lowered. The method adopting the environment-friendly raw materials which are low in cost is simple in synthetic process and higher in yield.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of 7-aminoceftrizime. Background technique [0002] The chemical name of ceftriaxone sodium is (6R,7R)-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[[(1, 2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio[methyl]-5-thio-1-nitro Heterobicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt triple hemihydrate. Ceftriaxone sodium is a third-generation cephalosporin antibiotic with broad-spectrum and high-efficiency characteristics. It is used for urinary tract, biliary tract infection, lower respiratory tract infection, pelvic infection, abdominal infection, bone and joint infection caused by sensitive pathogenic bacteria. Infection, skin and soft tissue infection, sepsis, meningitis and other diseases. [0003] Ceftriaxone sodium was successfully developed by Swiss Roche Company in 1978. After its patent expired in 1996, ceftriaxo...

Claims

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Application Information

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IPC IPC(8): C07D501/18C07D501/04
CPCC07D501/04C07D501/18
Inventor 杜明霞张立明
Owner YIYUAN XINQUAN CHEM