Method for purifying cefotetan acid crude products

A technology of cefotetan acid and purification method, which is applied in the field of preparation and purification of cephalosporin intermediates, can solve the problems of no isomer removal method, long time consumption, restriction of industrial production of cefotetan raw materials, etc., so as to shorten the transformation time The effect of reaction time

Active Publication Date: 2010-10-27
YANGTZE RIVER PHARM GRP CO LTD +1
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Problems solved by technology

Because this method takes a long time and there is no effective isomer removal m

Method used

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  • Method for purifying cefotetan acid crude products
  • Method for purifying cefotetan acid crude products
  • Method for purifying cefotetan acid crude products

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Get the cefotetan acid crude product 20g (HPLC detection isomer content is 8.95% for washing purification, see figure 1 ), was added to a 250ml reaction flask, and then 80ml of ethanol was added, stirred, suspended and washed for 30min at 15°C, vacuum filtered, and the filter cake was detected by HPLC, and the isomer content was 8.41%. Add 80 ml of cyclohexane to the filter cake in the first step, stir and wash at the same temperature for 30 minutes, vacuum filter, and detect by HPLC of the filter cake, the isomer content is 3.26%. Then add 120ml methyl alcohol to the filter cake of the second step, stir and wash 30min under the same temperature, vacuum suction filtration, filter cake HPLC detection, isomer content is 0.62%, see figure 2 . The overall yield is about 48%.

Embodiment 2

[0024] Get the cefotetan acid crude product 20g (the content of HPLC detection isomer is 4.09% for washing purification, see image 3 ), was added to a 250ml reaction flask, and then 60ml of ethanol was added, stirred, suspended and washed for 30min at 15°C, vacuum filtered, and the filter cake was detected by HPLC, and the isomer content was 3.61%. Add 60 ml of cyclohexane to the filter cake in the first step, stir and wash at the same temperature for 30 min, vacuum filter, and detect by HPLC of the filter cake, the isomer content is 2.66%. Then add 80ml methanol to the filter cake of the second step, stir and wash at the same temperature for 30min, vacuum filtration, filter cake HPLC detection, isomer content is 0.95%, see Figure 4 . The yield is about 55%.

Embodiment 3

[0026] Get the cefotetan acid crude product 20g (the content of HPLC detection isomer is 2.98% for washing purification, see Figure 5 ), was added to a 250ml reaction flask, and then 40ml of ethanol was added, stirred, suspended and washed for 30min at 15°C, vacuum filtered, and the filter cake was detected by HPLC, and the isomer content was 2.62%. Add 40ml of cyclohexane to the filter cake in the first step, stir and wash at the same temperature for 30min, vacuum filter, filter cake HPLC detection, the isomer content is 1.5%. Then add 40ml methanol to the filter cake of the second step, stir and wash at the same temperature for 30min, vacuum filtration, filter cake HPLC detection, isomer content is 0.36%, see Figure 6 . The yield is about 57%.

[0027] From the results shown in the above examples and accompanying drawings, it can be seen that the present invention can wash and purify cefotetan acid crude products with different isomer contents to meet the required purity...

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Abstract

The invention provides a method for purifying cefotetan acid crude products. The method comprises the following step of: stirring and washing the cefotetan acid crude products, which differ from one another in the isomer content, by taking ethanol, cyclohexane and methanol as solvents in turn and by using a suspension method at room temperature; and thus obtaining cefotetan acid of which the isomer content is less than 1 percent. The method has the advantages that: the isomer content of the cefotetan acid crude product is not limited clearly and a crude product of which the isomer content is high can also be purified completely; mother liquor left after washing is concentrated and can be recycled in an isomerization reaction, so that reaction time is shortened greatly without affecting total yield due to material recycling; and purification operation is performed at room temperature, operation is simple and convenient and mass production is performed easily.

Description

technical field [0001] The present invention relates to the preparation and purification method of cephalosporin intermediate, more specifically, relates to the purification method of cefotetan acid crude product. Background technique [0002] Antibiotics have played an extremely important role in the fight against infectious diseases in humans. According to statistics, my country's antibiotic drugs account for 14% of the total drug sales market share, ranking first among all types of drugs. Cephalosporin antibiotics in China emerged in the early 1980s, developed rapidly in the mid-1990s, and still maintained a vigorous development trend in the 21st century. [0003] Cefotetan (Cefotetan) is a second-generation cephalosporin antibiotic developed by Japan's Yamanouchi Pharmaceutical. In the process of preparation, it needs to undergo a reaction of isomer conversion, and the reaction formula is as follows: [0004] [0005] The isomer conversion reaction conditions are: ...

Claims

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Application Information

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IPC IPC(8): C07D501/57C07D501/12A61P31/04
Inventor 王超暮春明祝修权叶超曹志云袁会峰江涌储结根杨俊
Owner YANGTZE RIVER PHARM GRP CO LTD
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