A kind of synthetic method of 11α-chloromethyloxytetracycline p-toluenesulfonate

A technology of oxytetracycline chloramphenicol and p-toluenesulfonate, which is applied in the preparation of sulfonate, chemical instruments and methods, and preparation of carboxylic acid amide, which can solve the problems of environmental pollution and high production cost, and achieve safety High, low cost, simple production process

Active Publication Date: 2022-08-09
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the shortcomings of the original production process, such as serious environmental pollution and high production costs, this is the main reason why other countries in the world no longer produce this variety.

Method used

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  • A kind of synthetic method of 11α-chloromethyloxytetracycline p-toluenesulfonate
  • A kind of synthetic method of 11α-chloromethyloxytetracycline p-toluenesulfonate
  • A kind of synthetic method of 11α-chloromethyloxytetracycline p-toluenesulfonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A kind of synthetic method of 11α-chloromethytetracycline p-toluenesulfonate, comprising the following steps:

[0023] (1) Dehydration reaction: add 150g oxytetracycline and 93.92g anhydrous p-toluenesulfonic acid (that is, chloroxytetracycline and anhydrous p-toluenesulfonic acid) in a 1000ml autoclave equipped with a thermometer, stirring and pressure gauge The molar ratio of acid is 1:1.8), feed 500.48g supercritical carbon dioxide (that is, the molar ratio of chloroxytetracycline and supercritical carbon dioxide is 1:37.5), adjust the temperature to 32°C, control the pressure at 7.4MPa, and keep the temperature Stir for 5h to 8h to obtain 11α-chloromethyoxytetracycline.

[0024] (2) Salt-forming reaction: after the heat preservation is completed, the pressure is released, the temperature is lowered to 23 °C, and 600 g of anhydrous ethanol is added to the autoclave, and the temperature is kept at 23 °C and stirred for 9 hours. Drying in a vacuum oven at a low temper...

Embodiment 2

[0026] A kind of synthetic method of 11α-chloromethytetracycline p-toluenesulfonate, comprising the following steps:

[0027] (1) Dehydration reaction: add 150g oxytetracycline and 78.25g anhydrous p-toluenesulfonic acid (that is, chloroxytetracycline and anhydrous p-toluenesulfonic acid) in a 1000ml autoclave equipped with a thermometer, stirring and pressure gauge The molar ratio of acid is 1:1.5), feed 500.48g supercritical carbon dioxide (that is, the molar ratio of chloroxytetracycline and supercritical carbon dioxide is 1:37.5), adjust the temperature to 32°C, control the pressure at 7.4MPa, and keep the temperature Stir for 5h to 8h to obtain 11α-chloromethyoxytetracycline.

[0028] (2) After the heat preservation of the salt-forming reaction was completed, the pressure was released, the temperature was lowered to 23 °C, and 600 g of absolute ethanol was added to the autoclave, and the temperature was kept at 23 °C and stirred for 9 hours. Drying in a vacuum oven at a ...

Embodiment 3

[0030] A kind of synthetic method of 11α-chloromethytetracycline p-toluenesulfonate, comprising the following steps:

[0031] (1) Dehydration reaction: add 150g oxytetracycline and 93.92g anhydrous p-toluenesulfonic acid (that is, chloroxytetracycline and anhydrous p-toluenesulfonic acid) in a 1000ml autoclave equipped with a thermometer, stirring and pressure gauge The molar ratio of acid is 1:1.8), feed 500.48g supercritical carbon dioxide (that is, the molar ratio of chloroxytetracycline and supercritical carbon dioxide is 1:37.5), adjust the temperature to 32°C, control the pressure at 7.4MPa, and keep the temperature Stir for 5h to 8h to obtain 11α-chloromethyoxytetracycline.

[0032] (2) Salt-forming reaction: after the heat preservation is completed, the pressure is released, the temperature is lowered to 23 °C, and 600 g of anhydrous ethanol is added to the autoclave, and the temperature is kept at 23 °C and stirred for 9 hours. Drying in a vacuum oven at a low temper...

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Abstract

The invention discloses a method for synthesizing 11α-chloromethyoxytetracycline-p-toluenesulfonate, which solves the problems of unreasonable preparation method, high toxicity of raw materials, complicated operation, high cost, large output of three wastes and high yield. The technical problem of low and unsuitable for industrialized production, the present invention takes chloroxytetracycline as raw material, takes supercritical carbon dioxide as reaction solvent, takes anhydrous p-toluenesulfonic acid as dehydrating agent, and generates 11α-chloromethane through dehydration reaction Oxytetracycline, and then take absolute ethanol as a reaction solvent to generate a salt-forming reaction to obtain 11α-chloromethyoxytetracycline p-toluenesulfonate. The invention can be widely used in the technical field of veterinary medicine.

Description

technical field [0001] The present application belongs to the technical field of 11α-chloromethylene oxytetracycline synthesis, and more specifically relates to a 11α-chloromethylene oxytetracycline p-toluenesulfonate. Background technique [0002] 11α-Chloromethyoxytetracycline p-toluenesulfonate, its structural formula is as follows: [0003] [0004] 11α-Chloromethytetracycline is an important intermediate product in the production of doxycycline (doxycycline hydrochloride), which is obtained from chloroxytetracycline through dehydration reaction. Doxycycline hydrochloride is a good antibacterial drug. It is a long-acting broad-spectrum semi-synthetic tetracycline antibiotic made from oxytetracycline. It has a wide antibacterial spectrum and strong antibacterial effect. In addition to the effect on Gram-positive bacteria and negative bacteria, it can also inhibit Rickettsia, Mycoplasma pneumoniae, Mycoplasma trachomatis, Amoeba, etc. In particular, the common bacteri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/12C07C237/26C07C303/32C07C309/30
CPCC07C231/12C07C303/32C07C2603/46C07C237/26C07C309/30Y02P20/54
Inventor 刘聪王伟宏王金辉张建强郭兴龙
Owner SHANDONG GUOBANG PHARMA
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