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Preparation method of optically active ornidazole

An optically active, ornidazole technology, applied in the field of organic chemical synthesis, can solve the problems of high cost and difficult three-waste treatment, and achieve the effects of low cost, few types of solvents, and reduced pollution

Pending Publication Date: 2020-12-25
SHIJIAZHUANG NO 4 PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aiming at the problems of high cost, difficulty in the treatment of three wastes, or the need for low-temperature reaction in the current preparation technology of left-ornidazole and its enantiomers, the present invention provides an improved preparation method of optically active ornidazole

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The present embodiment provides a kind of preparation method of levonidazole:

[0021] Add 1L of 85% (v / v) formic acid to a 2L reaction flask, add 60ml of 98% (m / v) concentrated sulfuric acid and 200g of 2-methyl-5-nitroimidazole under stirring, control the reaction temperature at 30-40°C, drop Add 307ml of S-(+)-epichlorohydrin, after the dropwise addition, react at 30-40°C for 4.5h, then cool down to 5°C, adjust the pH to 2.5 with ammonia water, filter, and recover 2-methyl-5-nitrate Kiimidazole 59.4g. The filtrate was extracted with ethyl acetate (700ml×3), the ethyl acetate phases were combined, extracted with 50% (m / v) sulfuric acid aqueous solution (200ml×3), the 50% (m / v) sulfuric acid aqueous solution was combined, and adjusted with ammonia water. When the pH reached 7.5, levonidazole solid was precipitated, filtered, and dried to obtain 201.6 g of levonidazole crude product;

[0022] Get 201.6g of the crude product of levonidazole, add 2L of water, after heat...

Embodiment 2

[0024] Add 1L of 85% (v / v) formic acid to a 2L reaction flask, add 60ml of 98% (m / v) concentrated sulfuric acid and 200g of 2-methyl-5-nitroimidazole under stirring, control the reaction temperature at 30-40°C, drop Add 307ml of R-(-)-epichlorohydrin, after the dropwise addition, react at 30-40°C for 4.5h, then cool down to 5°C, adjust the pH to 2.5 with ammonia water, filter, and recover 2-methyl-5-nitrate Kiimidazole 59.2g. The filtrate was extracted with ethyl acetate (700ml×3), the ethyl acetate phases were combined, extracted with 50% (m / v) sulfuric acid aqueous solution (200ml×3), the 50% (m / v) sulfuric acid aqueous solution was combined, and adjusted with ammonia water. When the pH reached 7.5, dex-ornidazole solid was precipitated, filtered, and dried to obtain 202.1 g of dex-ornidazole crude product;

[0025] Take 202.1 g of the crude product of dex-ornidazole and 2 L of water, heat to dissolve, add 0.5% activated carbon for decolorization for 30 minutes, heat filter...

Embodiment 3

[0027] The present embodiment provides a kind of preparation method of levonidazole:

[0028] Add 1L of 85% (v / v) formic acid to a 2L reaction flask, add 80ml of 98% (m / v) concentrated sulfuric acid and 200g of 2-methyl-5-nitroimidazole under stirring, control the reaction temperature at 30-40°C, drop Add 307ml of S-(+)-epichlorohydrin, after the dropwise addition, react at 30-40°C for 5 hours, then cool down to 10°C, adjust the pH to 2.5 with ammonia water, filter, and recover 2-methyl-5-nitro Imidazole 59.6g. The filtrate was extracted with ethyl acetate (700ml×3), the ethyl acetate phases were combined, extracted with 50% (m / v) sulfuric acid aqueous solution (200ml×3), the 50% (m / v) sulfuric acid aqueous solution was combined, and adjusted with ammonia water. When the pH reached 7.5, a solid levonidazole was precipitated, filtered, and dried to obtain 201.2 g of the crude product of levonidazole;

[0029] Take 201.2g of the crude product of levonidazole, add 1600ml of wat...

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Abstract

The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of optically active ornidazole. According to the preparation method, 2-methyl-5-nitroimidazole and optically active epoxy chloropropane are used as raw materials, an acid solvent is used as a reaction solvent, Lewis acid is used as a catalyst, a reaction is carried out under the condition close to normal temperature, and then extraction is carried out to obtain the product. Compared with the traditional optically active ornidazole synthesis process, the preparation method has theadvantages that the use of aluminum trichloride is avoided, the pollution of aluminum salt to the environment is reduced, low-temperature control in the reaction process is not needed, the reaction conditions are mild and easy to control, the temperature control cost can be reduced, the types of solvents are fewer, the operation is simple, and the cost is lower; and the method is suitable for industrial production of optically active ornidazole.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of optically active ornidazole. Background technique [0002] Ornidazole (ornidazole), the chemical name is 2-methyl-1-(3-chloro-2-hydroxypropyl)-3-nitro-1H-imidazole, is a powerful anti-anaerobe and anti-protozoal infection drug, It is also the third-generation nitroimidazole derivative with higher curative effect, shorter course of treatment, better tolerance and wider distribution in the body than metronidazole. The commercially available ornidazole is mainly racemic. Clinical trials have found that the pharmacokinetics of left ornidazole is superior to that of right ornidazole and racemic ornidazole, and its central toxicity is lower than that of right ornidazole and racemic Ornidazole, so the use of left-ornidazole for the preparation of anti-anaerobic infection drugs has more applicability. The preparation technology of ...

Claims

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Application Information

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IPC IPC(8): C07D233/94
CPCC07B2200/07C07D233/94
Inventor 孙立杰刘少倩赵世雄穆鸿岳石红超庞志杰白雪
Owner SHIJIAZHUANG NO 4 PHARMA
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