Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation and purification method for optical enantiomer of ornidaxole

An ornidazole optical and enantiomeric technology is applied in the field of preparation and purification of ornidazole optical enantiomer, and can solve the problem of many side reactions of chiral ethylene oxide, low yield, and optical enantiomer of ornidazole. problems such as large body cost, to achieve the effects of high yield, simple operation and mild reaction conditions

Active Publication Date: 2008-03-19
XIAN TIANYI QINKUN PHARMA
View PDF2 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One is splitting by enzymatic method, see Chinese patent CN1400312A, the cost required by this method to obtain the optical enantiomer of ornidazole is relatively large, and it is not suitable for large-scale production; the other method is disclosed in Chinese patent 200510127033.3, this reaction The process is simple, the reaction steps are few, and the disadvantage is that there are many side reactions of chiral ethylene oxide and the yield is low

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation and purification method for optical enantiomer of ornidaxole
  • Preparation and purification method for optical enantiomer of ornidaxole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] a. Preparation of nitroimidazole methyl acetate

[0019] Mix 30kg of 2-methyl-5-nitroimidazole, 41kg of anhydrous sodium carbonate, 200L of ethyl acetate and a small amount of phase transfer catalyst in a 500L enamel reaction kettle, slowly add 40kg of chloromethyl acetate, and heat to Reflux for 7 hours, cool to room temperature, filter, wash with water, add anhydrous sodium sulfate to dry, recover ethyl acetate to dryness, and obtain 56 kg of nitroimidazolium acetate.

[0020] b. Preparation of Cyclic Sulfate

[0021] Dissolve 110kg of S-3-chloro-1,2-propanediol in 500L of methylene chloride in a 1000L enamel reaction kettle, add dropwise a mixed solution of 200kg of thionyl chloride and 100L of methylene chloride under cooling with ice-salt water, and after the addition is completed, liter High temperature to reflux, react for 1.5 hours. Cool to -10°C-0°C, then slowly add 100L of 30% hydrogen peroxide, keep warm at 0-10°C for 3 hours, separate liquid, wash with wat...

Embodiment 2

[0025] c. Preparation of nitroimidazole methyl acetate

[0026] Mix 25kg of 2-methyl-5-nitroimidazole, 37kg of anhydrous sodium carbonate, 150L of acetonitrile and a small amount of phase transfer catalyst in a 300L enamel reaction kettle, slowly add 40kg of chloromethyl acetate, and heat to reflux for 6 hours, filter, recover acetonitrile, dissolve the residue with ethyl acetate, wash with water, add anhydrous sodium sulfate to dry, recover ethyl acetate to dryness, and obtain 46.1 kg of nitroimidazolium acetate.

[0027] d. Preparation of Cyclic Sulfate

[0028] Dissolve 110kg of R--3-chloro-1,2-propanediol in 500L of dichloromethane in a 1000L enamel reaction kettle, and add dropwise a mixed solution of 200kg of thionyl chloride and 100L of dichloromethane under cooling with ice-salt water. After the addition is complete, Raise the temperature to reflux and react for 1.5 hours. Cool to -10°C-0°C, then slowly add 100L of 30% hydrogen peroxide, keep warm at 0-10°C for 3 hou...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation and purification method of ornidazole optical enantiomer. Under suitable conditions, chloromethyl acetate reacts with 2-cymene-5 nitro imidazole in order to acquire nitro acetate imidazole methyl ester; chiral 3-chlorine-1, 2 propanediol reacts with thionyl chloride, and the obtained product is oxygenated, so that chiral cyclic sulfate is produced; finally, the nitro acetate imidazole methyl ester reacts with the chiral cyclic sulfate to generate a product, which is hydrolyzed to obtain the corresponding ornidazole optical enantiomer. The invention has the advantages of convenient operation and high purity of products and is applied to industrial production.

Description

Technical field: [0001] The invention relates to a method for preparing and purifying optical antipodes of ornidazole. technical background: [0002] Ornidazole is (( + ) 1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (Ornidazole, CAS16773-42-5). Ornidazole is a nitroimidazole derivative, which is a powerful drug against anaerobic bacteria and antiprotozoal infection. Broader third-generation nitroimidazole derivatives. The antimicrobial effect of ornidazole is through the reduction of the nitro group in its molecule to an amino group in an oxygen-free environment, or through the formation of free radicals to interact with cell components, resulting in the death of microorganisms. There are two prior art methods for preparing the optical antipodes of ornidazole. One is splitting by enzymatic method, see Chinese patent CN1400312A, the cost required by this method to obtain the optical enantiomer of ornidazole is relatively large, and it is not suitable for large-s...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D233/94
Inventor 苏红军强建华
Owner XIAN TIANYI QINKUN PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com