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Method for catalytically synthesizing doxycycline dehydrated substance by using ionic liquid and zeolite at normal temperature

A technology of ionic liquid and doxycycline, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., to achieve the effect of less by-products, mild reaction conditions and high yield

Active Publication Date: 2022-04-12
扬州联博药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, there have also been reports of using other dehydrating agents such as thionyl chloride, but none of them can change a dilemma. The maintenance of equipment and the non-toxic treatment of waste acid are headaches for major pharmaceutical companies.

Method used

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  • Method for catalytically synthesizing doxycycline dehydrated substance by using ionic liquid and zeolite at normal temperature
  • Method for catalytically synthesizing doxycycline dehydrated substance by using ionic liquid and zeolite at normal temperature

Examples

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Effect test

Embodiment 1

[0024] A method for catalytically synthesizing doxycycline dehydrate with normal temperature ionic liquid and zeolite, comprising the following steps:

[0025] a) Weigh 43.6 g of 3-sulfobutyl-1-methylimidazolium, slowly add 30.2 g of trifluoromethanesulfonic acid, stir thoroughly for 1 hour, and obtain 73.9 g of viscous liquid;

[0026] Immerse 5g of H-beta zeolite with 10mL of 0.1mol / L disodium citrate solution, stir for 5 hours under the condition of heating in a water bath at 70°C, and repeat twice after suction filtration to obtain about 5g of citrate-modified H-beta zeolite ; 50 mg of citrate-modified H-beta zeolite was added to 50 mL of 3-sulfobutyl-1-isopropylimidazolium-trifluoromethanesulfonic acid ionic liquid at 20°C and stirred for 5 min to form Ionic liquid reaction system;

[0027] b) Put 25 g of dried oxytetracycline into the above-mentioned ionic liquid reaction system at 20°C, stir to dissolve, keep the temperature at 23°C for 70 minutes, and recover the zeol...

Embodiment 2

[0031] A method for catalytically synthesizing doxycycline dehydrate with normal temperature ionic liquid and zeolite, comprising the following steps:

[0032] a) Weigh 1.85 kg of 3-sulfobutyl-1-ethylimidazolium, slowly add 0.77 kg of methanesulfonic acid, and fully stir for one hour to obtain 2.64 kg of viscous liquid;

[0033] Immerse 100g of H-beta zeolite with 0.2L of 0.15mol / L potassium dihydrogen phosphate solution, stir for 5 hours under the condition of heating in a water bath at 80°C, and repeat twice after suction filtration to obtain about 100g of phosphate-modified H-beta zeolite ; Add 20g of phosphate-modified H-beta zeolite to 2L of 3-sulfobutyl-1-ethylimidazolium-trifluoromethanesulfonic acid ionic liquid at 20°C and stir for 10min to form an ionic liquid reaction system;

[0034] b) Put 1kg of dried oxytetracycline into the above-mentioned ionic liquid reaction system at 20°C, stir and dissolve, keep the temperature at 23°C for 70 minutes, and recover the zeol...

Embodiment 3

[0038] A method for catalytically synthesizing doxycycline dehydrate with normal temperature ionic liquid and zeolite, comprising the following steps:

[0039] a) Weigh 984.4 kg of 3-sulfobutyl-1-isopropylimidazolium, slowly add 600.3 kg of trifluoromethanesulfonic acid, and stir thoroughly for 1 hour to obtain 1585.4 kg of viscous liquid;

[0040] Immerse 1kg of H-beta zeolite with 10L of 0.1mol / L potassium dihydrogen phosphate solution, stir for 5h under the condition of heating in a water bath at 70°C, and repeat twice after suction filtration to obtain about 1kg of phosphate-modified H-beta zeolite; Add 1kg of phosphate-modified H-beta zeolite to 1000L 3-sulfobutyl-1-isopropylimidazolium-trifluoromethanesulfonic acid ionic liquid at 20°C, stir for 30 minutes, and form an ionic liquid reaction system;

[0041]b) Put 500 kg of dried oxytetracycline into the above-mentioned ionic liquid reaction system at 20° C., stir and dissolve, and keep the reaction at 23° C. for 70 minu...

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Abstract

The invention discloses a method for catalytically synthesizing a doxycycline dehydrated substance by using a normal-temperature ionic liquid and zeolite, and belongs to the technical field of production of doxycycline intermediates. The method comprises the following steps: a) mixing imidazole inner salt and protonic acid to synthesize ionic liquid; adding a zeolite catalyst into the ionic liquid, and uniformly stirring and mixing to form an ionic liquid reaction system; b) adding chloro-oxytetracycline into the ionic liquid reaction system, stirring and dissolving for reaction, and filtering and recovering the zeolite catalyst after the reaction is finished; c) adding the reaction solution into a p-toluenesulfonic acid ethanol solution at a constant speed, stirring and crystallizing, filtering after crystallization, and carrying out solid-liquid separation to obtain a dehydrated substance p-toluenesulfonate; the ionic liquid is recovered through liquid separation and evaporation. The method is mild in reaction condition, and almost no waste water or waste acid is generated; and the prepared doxycycline dehydrated product has the advantages of less by-products and high yield.

Description

technical field [0001] The invention belongs to the technical field of production of doxycycline intermediates, and in particular relates to a method for catalytically synthesizing doxycycline dehydrate with normal temperature ionic liquid and zeolite. Background technique [0002] Doxycycline, chemical formula C 22 h 24 N 2 o 8 , the chemical name is 6-methyl-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6, 11,12a-Octahydro-2-tetracenecarboxamide, yellow crystal at room temperature, belongs to tetracyclic antibiotics clinically, and has good clinical effect. It is mainly used for upper respiratory tract infection, tonsillitis, biliary tract infection, lymphadenitis, cellulitis, senile chronic bronchitis, etc. caused by sensitive gram-positive cocci and gram-negative bacilli. It is also used for typhus, scrub typhus, Mycoplasma pneumonia, etc. It can still be used to treat cholera, and also to prevent falciparum malaria and Leptospirosis infection...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/26
CPCY02P20/584Y02A50/30
Inventor 章留留王天池陈佳业倪再欣张亚蕾张富荣
Owner 扬州联博药业有限公司
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