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

Preparation method for optical enantiomer of ornidaxole

An ornidazole optical and enantiomer technology is applied in the field of preparation of ornidazole optical enantiomer, can solve problems such as being unsuitable for industrial production, and achieves the effects of simple method, easy-to-obtain raw materials and strong stereospecificity

Active Publication Date: 2008-02-13
HUNAN WARRANT PHARMA +1
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method report of preparing ornidazole optical antipodes is less, and CN1212405 has reported the method that utilizes enzymatic resolution to obtain optically pure ornidazole from the racemate of ornidazole, but this method is not suitable for suitability for industrialized production

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 method for optical enantiomer of ornidaxole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of S-(-)-ornidazole: Add 50.8 g (0.4 mol) of 2-methyl-5-nitroimidazole into 500 mL of ethyl acetate, and cool to 0-5°C. Add 80.1 g (0.6 mol) of anhydrous aluminum trichloride in batches, and control the reaction temperature not higher than 10°C. After the addition is complete, 55.5 g (0.6 mol) of S-(+)-epichlorohydrin is added dropwise to the reaction solution at 0-10°C, and the reaction is continued at 0-10°C for 4 hours after the drop is completed. After the reaction is complete, slowly add 200 mL of ice water to the reaction solution, control the temperature of the reaction solution to be lower than 30°C, stir for 1 hour, filter, add 50% sulfuric acid dropwise to the filtrate, adjust the pH to 1.0, and then add concentrated Adjust the pH to 3-4 with ammonia water, precipitate solids, filter, and adjust the pH of the obtained filtrate to 7.0-7.5 with concentrated ammonia water, separate the ethyl acetate layer, dry with anhydrous sodium sulfate, evaporate ...

Embodiment 2

[0022] Preparation of S-(-)-ornidazole: In 450 mL of dichloromethane, add 50.8 g (0.4 mol) of 2-methyl-5-nitroimidazole, and cool to 0-5°C. Add 80.1 g (0.6 mol) of anhydrous zinc chloride in batches, and control the reaction temperature not higher than 10°C. After the addition is complete, 55.5 g (0.6 mol) of S-(+)-epichlorohydrin is added dropwise to the reaction solution at 0-10°C, and the reaction is continued at 0-10°C for 6 hours after the addition is completed. After the reaction, 200 mL of ice water was slowly added to the reaction solution, the temperature of the reaction solution was controlled to be lower than 30° C., stirred for 1.5 hours, filtered, and the filtrate was added dropwise with 50% sulfuric acid to adjust the pH to 0.5. Then, dropwise added three Ethylamine was adjusted to pH 3-4, solid precipitated, filtered, and the resulting filtrate was adjusted to pH 7.0-7.5 with triethylamine, the dichloromethane layer was separated, dried with anhydrous magnesium ...

Embodiment 3

[0024] Preparation of R-(+)-ornidazole: Add 50.8 g (0.4 mol) of 2-methyl-5-nitroimidazole into 500 mL of ethyl acetate, and cool to 0-5°C. Add 80.1 g (0.6 mol) of anhydrous aluminum trichloride in batches, and control the reaction temperature not higher than 10°C. After the addition is complete, 55.5 g (0.6 mol) of R-(-)-epichlorohydrin is added dropwise to the reaction solution at 0-10°C, and the reaction is continued at 0-5°C for 5 hours after the drop is complete. After the reaction, slowly add 200 mL of ice water into the reaction liquid, control the temperature of the reaction liquid below 30°C, stir for 0.5 hours, filter, add hydrochloric acid dropwise to the filtrate, adjust the pH to 1.0, and then add concentrated ammonia water dropwise to the mixed liquid to adjust When the pH reached 3-4, solids were precipitated, filtered, and the obtained filtrate was adjusted to pH 7.0-7.5 with concentrated ammonia water, and the ethyl acetate layer was separated, dried with anhyd...

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 discloses a preparing method of naxogin optical antimer, which comprises the following steps: adopting 2-methyl-5-nitroglyoxalinyl and S-(+)-epichlorohydrin or R-(-)-epichlorohydrin as raw material; reacting to obtain S-(-)-naxogin or R-(+)-naxogin catalyzed by Lewis acid in the organic solvent; obtaining the product with purity over 99.5%.

Description

technical field [0001] The invention relates to a preparation method of ornidazole optical antipodes, belonging to the field of chemical synthesis. Background technique [0002] Ornidazole (ornidazole), the chemical name is 2-methyl-1-(3-chloro-2-hydroxypropyl)-3-nitro-1H-imidazole, is a good anti-anaerobe and antiprotozoal 5- Nitroimidazole antibiotics are currently marketed and clinically applied as racemates. There are few reports on the preparation of optical enantiomers of ornidazole. CN1212405 reports a method for obtaining optically pure ornidazole from the racemate of ornidazole by enzymatic resolution, but this method is not suitable for industrial production. Contents of the invention [0003] The purpose of the present invention is to provide a preparation method of ornidazole optical antipodes, and further to provide a preparation method of S-(-)-ornidazole or R-(+)-ornidazole. [0004] The preparation method of the present invention uses 2-methyl-5-nitroimid...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/94
Inventor 史秀兰谢安云
Owner HUNAN WARRANT 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