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Preparation method of metacycline

The technology of metacycline and methicillin, which is applied in the field of veterinary medicine, can solve the problems of complex catalyst preparation method, high catalyst preparation cost, excessive metal content in products, etc., and achieves simple selection of reaction equipment and high selectivity. , the effect of safe reaction conditions

Active Publication Date: 2021-03-12
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003]The current preparation method of metacycline is the reductive dechlorination of 11α-chloro-6-methine oxytetracycline p-toluenesulfonate by heterogeneous catalysis This type of method generally uses catalysts containing active components such as noble metal palladium and ruthenium. The preparation methods of these catalysts are relatively complicated, and it is difficult to control the activity of the prepared catalysts.
And when palladium is used as the active component, the price of palladium is very expensive, and the catalyst preparation cost is very high; when using cheaper ruthenium, ruthenium is easy to lose in the acidic environment of dechlorination, the catalyst cannot be applied mechanically and the metal loss causes the metal content of the product to exceed the standard

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1 prepares dechlorination reagent sodium trimethoxyborohydride

[0033] Check the airtightness of the 500ml reaction bottle, add 300.14g of dichloromethane into the reaction bottle, and the water content of the dichloromethane is lower than 0.1%. Dichloromethane was cooled to 0-5°C, 50.11g of trimethyl borate was added to the reaction flask, stirred and dissolved, 9.50g of sodium hydride was added to the reaction flask, the reaction flask was sealed, and the temperature was controlled at 0-5°C for 16-24h. Filter to obtain 63.28g of sodium trimethoxyborohydride wet product, control the wet product at 10-15°C, bake under reduced pressure to constant weight, and obtain 48.16g of sodium trimethoxyborohydride, with a detection content of 99.4% and a moisture content of 0.01%. The yield was 94.52%.

Embodiment 2

[0036] Put 99.97g of solvent 45% ethanol water into a 500ml reaction bottle equipped with a thermometer and mechanical stirring, put in 20.05g of 11α-chloro-6methine oxytetracycline p-toluenesulfonate, control the temperature at 25°C, and divide it into 8 times Add 5.40 g of the dechlorination reagent prepared above, and add sodium trimethoxyborohydride for 150 minutes. After the addition, the mixture was stirred and reacted for 3 hours, and a sample was taken for liquid phase analysis. The conversion rate was 98.6%, the selectivity was 92.1%, and the yield was 90.8%.

Embodiment 3

[0038] Put 99.79g of solvent 45% ethanol water into a 500ml reaction bottle equipped with a thermometer and mechanical stirring, put in 20.13g of 11α-chloro-6methine oxytetracycline p-toluenesulfonate, control the temperature at 20°C, and divide it into 8 times Add 5.44 g of the dechlorination reagent prepared above, and add sodium trimethoxyborohydride for 150 minutes. After the addition, the mixture was stirred and reacted for 3 hours, and the liquid phase analysis was carried out by sampling. The conversion rate was 97.5%, the selectivity was 95.7%, and the yield was 93.3%.

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PUM

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Abstract

The invention provides a preparation method of metacycline. The metacycline is prepared by carrying out dechlorination reaction on 11alpha-chloro-6-methyleneoxytetracycline p-toluenesulfonate under the action of a dechlorinating agent. The product prepared by the method is high in selectivity and yield, the yield of the metacycline is 90.8-98.6 percent, reaction conditions are very mild and safe,and reaction equipment model selection is relatively simple; on the other hand, the preparation of the dechlorination reagent is relatively simple, the reaction process is relatively simple, and the production cost is greatly reduced.

Description

technical field [0001] The invention relates to the technical field of veterinary medicine, in particular to a preparation method of metacycline, an intermediate of doxycycline. Background technique [0002] Metacycline is a tetracycline antibiotic. Some strains resistant to tetracycline or oxytetracycline are still sensitive to metacycline. Many rickettsia, mycoplasma, chlamydia, some atypical mycobacteria, and spirochetes are sensitive to this product. Others such as Actinomycetes, Bacillus anthracis, Listeria monocytogenes, Clostridium, Nocardia, Vibrio, Brucella, Campylobacter, Yersinia, etc. are sensitive to this product. This product has certain antibacterial activity against Neisseria gonorrhoeae. It has strong antibacterial activity against Gram-positive or negative bacteria; it can be used for rickettsiasis, mycoplasma pneumonia, lymphogranuloma, chancre, plague, cholera, brucellosis (combined application with streptomycin), etc. It is also effective against sys...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/26C07C303/32C07C309/30C07F5/04
CPCC07C231/12C07C303/32C07F5/04C07C2603/46C07C237/26C07C309/30Y02A50/30
Inventor 刘聪郭兴龙杨俊德达先鹏王伟宏
Owner SHANDONG GUOBANG PHARMA
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