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Synthetic method of cefbuperazone intermediate

A technology for cefrazone and a synthesis method, which is applied in the field of synthesis of cefrazone intermediates, can solve the problems of non-compliance with environmental protection requirements, difficulty in separation and purification, and many reaction steps, and achieves low cost, high yield and convenient preparation. Effect

Active Publication Date: 2016-10-26
CHENGDU BAISHIXING SCI & TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The above process scheme has many reaction steps, cumbersome operation, difficult separation and purification, and does not meet environmental protection requirements

Method used

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  • Synthetic method of cefbuperazone intermediate

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Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: a kind of synthetic method of cefbuperazone intermediate, cefbuperazone intermediate is at normal temperature D-threonine and N-ethyl-2,3-dioxopiperazinyl formyl chloride in alkaline Directly react in the solvent to generate, after the reaction is completed, the layers are separated, the lower layer of the water layer is extracted with dichloromethane to extract small polar impurities, the pH value of the water phase is adjusted to 0 with concentrated hydrochloric acid and concentrated to dryness, dissolved in ethyl acetate as a desalting solvent and After filtration, the filtrate was concentrated to dryness, and then dichloromethane was added at 20°C for slurry purification to obtain the purified cefbuperazone intermediate.

[0027] Wherein, the equivalent ratio of D-threonine and N-ethyl-2,3-dioxopiperazinylcarbonyl chloride is 1:1; the normal temperature is 20°C; the alkali is sodium hydroxide; The solvent is water; the mass volume ratio of the solvent ...

Embodiment 2

[0028] Embodiment 2: a kind of synthetic method of cefbuperazone intermediate, cefbuperazone intermediate is at normal temperature D-threonine and N-ethyl-2,3-dioxopiperazinyl formyl chloride in alkaline It is formed by direct reaction in the solvent. After the reaction is completed, the layers are separated. The lower water layer is extracted with dichloromethane to extract small polar impurities. The pH value of the water phase is adjusted to 6 with concentrated sulfuric acid and concentrated to dryness. After the filtrate was concentrated to dryness, chloroform was added at 80°C for beating and purification to obtain the purified cefbuperazone intermediate.

[0029] Wherein, the equivalent ratio of D-threonine and N-ethyl-2,3-dioxopiperazinylcarbonyl chloride is 1:1.1; the normal temperature is 30°C; the base is potassium hydroxide; The solvent is a mixture of water and dichloromethane, and the volume ratio of dichloromethane to water is 1:10; the mass volume ratio of the s...

Embodiment 3

[0030] Embodiment 3: a kind of synthetic method of cefbuperazone intermediate, cefbuperazone intermediate is at normal temperature D-threonine and N-ethyl-2,3-dioxopiperazinyl formyl chloride in alkaline It is formed by direct reaction in the solvent. After the reaction is completed, the layers are separated. The lower aqueous layer is extracted with dichloromethane to extract small polar impurities. The pH value of the aqueous phase is adjusted to 1 with concentrated phosphoric acid and concentrated to dryness. Dissolve and filter with desalting solvent propionitrile After the filtrate was concentrated to dryness, ethyl acetate was added at 25°C for beating and purification to obtain the purified cefbuperazone intermediate.

[0031] Wherein, the equivalent ratio of D-threonine and N-ethyl-2,3-dioxopiperazinylformyl chloride is 1:1.2; the normal temperature is 22°C; the base is sodium carbonate; The solvent is a mixture of water and dichloromethane, and the volume ratio of dic...

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Abstract

The invention discloses a synthetic method of a cefbuperazone intermediate, belonging to the technical field of chemical synthesis. The cefbuperazone intermediate is prepared by virtue of direct reaction of D-threonine and N-ethyl-2,3-dioxopiperazinyl formyl chloride in an alkali solvent at the room temperature. The synthetic method has the beneficial effects that the synthesis can be finished only through one step, has low reaction requirements and can be carried out at the room temperature; optimally, a reaction solvent is dichloromethane and can be taken as a later-period purification solvent, so that the cost is saved; the yield is high, and the product purity can reach 99.8%; and the operation is simple, the preparation is convenient, the cost is low, and the synthetic method is applicable to large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthetic method of a cefbuperazone intermediate. Background technique [0002] Cefbuperazone is a third-generation cephalosporin antibiotic developed by Japan Toyama Chemical Industry Pharmaceutical Co., Ltd. in the 1970s and listed in 1985. As a cephalosporin derivative, cephradine has a similar mechanism of action to other cephalosporins. It mainly plays a bactericidal effect by inhibiting the synthesis of bacterial cell walls, and has a good antibacterial effect on Gram-negative bacteria and anaerobic bacteria. Due to the introduction of methoxy group at the 7th position, cefbuperazone increases the enzyme resistance, and its stability to β-lactamase is better than that of similar varieties. It has strong penetrating power, wide distribution in the body, and can reach therapeutic concentrations in many parts. . At present, there is no cefbuperazone ...

Claims

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Application Information

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IPC IPC(8): C07D241/08
CPCC07B2200/07C07D241/08
Inventor 石常青莫凡
Owner CHENGDU BAISHIXING SCI & TECH IND
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