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

Method for simply and efficiently preparing efavirenz intermediates

A technology of efavirenz and intermediates, which is applied in the field of organic compound catalytic chemistry, can solve the problems of low atom economy, high cost, complex synthesis operation, etc., and achieve the effect of wide application prospect and simple and efficient preparation

Inactive Publication Date: 2014-12-10
SHIHEZI UNIVERSITY
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Metal alkyne compounds need to be prepared with Grignard reagents or organolithium reagents, but these metal organic reagents are sensitive to water and oxygen, and the synthesis operations are complex and produce a large number of by-products
The second type of method uses trialkylsilyne and trifluoromethyl ketone as raw materials, but trialkylsilyne needs to be prepared through a two-step complex synthesis process, resulting in higher cost and lower atom economy (Tetrahedron Lett., 2006, 47, 8083-8086; J. Org. Chem., 2011, 76, 4482-4488.)
However, this method also has factors that limit its industrial application, such as the need for expensive, water- or oxygen-sensitive ligands

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
  • Method for simply and efficiently preparing efavirenz intermediates
  • Method for simply and efficiently preparing efavirenz intermediates
  • Method for simply and efficiently preparing efavirenz intermediates

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 2

[0017]

[0018] 2,2,2-trifluoroacetophenone (0.5mmol), 4-methylphenylacetylene (1.0mmol), CuCl (0.05mmol), Na 2 CO 3 (0.1mmol) and DMF (1mL) were added into a Schlinke bottle, stirred and reacted at 50°C for 24h, followed by TLC. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, the reaction mixture was extracted with dichloromethane (15 mL × 3) to extract the reaction product, the organic phases were combined, concentrated using a rotary evaporator to obtain a crude product, and the target product was obtained by column chromatography. The eluent used for analysis was petroleum ether: ethyl acetate (10:1), and the structure of the product was identified by NMR and high-resolution mass spectrometry. The separation yield reaches 94%.

specific Embodiment 3

[0019]

[0020] 2,2,2-trifluoroacetophenone (0.5mmol), 4-methoxyphenylacetylene (1.0mmol), Cu (0.05mmol), NaHCO 3 (0.1mmol) and toluene (1mL) were added into a Schlinke bottle, stirred and reacted at 50°C for 24h, followed by TLC. After the reaction was over, 15 mL of saturated brine was added to quench the reaction, the reaction mixture was extracted with dichloromethane (15 mL×3) to extract the reaction product, the organic phases were combined, concentrated using a rotary evaporator to obtain a crude product, and the target product was obtained by column chromatography. The eluent used for analysis was petroleum ether: ethyl acetate (10:1), and the structure of the product was identified by NMR and high-resolution mass spectrometry. The separation yield reaches 95%.

specific Embodiment 4

[0021]

[0022] 2,2,2-trifluoroacetophenone (0.5mmol), 4-ethylphenylacetylene (1.0mmol), Cu 2 O (0.05mmol), K 3 PO 4 .3H 2 O (0.1mmol) and NMP (1mL) were added into a Schlinke flask, and the reaction was stirred at 50°C for 24h, followed by TLC. After the reaction was over, 15 mL of saturated brine was added to quench the reaction, the reaction mixture was extracted with dichloromethane (15 mL×3) to extract the reaction product, the organic phases were combined, concentrated using a rotary evaporator to obtain a crude product, and the target product was obtained by column chromatography. The eluent used for analysis was petroleum ether: ethyl acetate (10:1), and the structure of the product was identified by NMR and high-resolution mass spectrometry. The separation yield reaches 97%.

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 relates to a method for simply and efficiently preparing efavirenz intermediates, which belongs to the technical field of organic compound catalytic chemistry. The method is used for the high-yield preparation of a series of efavirenz intermediates by taking copper as a catalyst and taking trifluoromethyl ketone and terminal alkyne as raw materials. The method is simple to operate and does not need any inert gas shielding; and the method is low in cost, and no extra ligand is added. Therefore, the method has a broad application prospect on the aspects of medicine, pesticides, synthesis of organic functional materials, and the like.

Description

technical field [0001] The invention relates to a simple and efficient method for preparing an efavirenz intermediate, which belongs to the technical field of organic compound catalytic chemistry. Background technique [0002] The addition reaction of trifluoromethyl ketone and terminal alkyne is widely used in the synthesis of drugs, pesticides and organic functional materials. There are two reasons why this type of reaction is important: (1) there is an acetylenic bond in the product, which can be further Functionalization, so it is an important class of organic synthesis intermediates; (2) while forming a carbon-carbon, introduce a CF into the target molecule 3 This is a group with potential biological activity and special physical properties, because 30% of the drugs and 20% of the pesticides currently synthesized contain fluorine atoms. Among them, this kind of compound is an important intermediate for preparing the specific anti-HIV drug efavirenz. [0003] Currently...

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 Applications(China)
IPC IPC(8): C07B41/02C07C33/48C07C29/42C07C33/50C07C43/23C07C41/30C07D333/16C07C69/732C07C67/343C07C215/68C07C213/00
Inventor 刘宁代斌王磊
Owner SHIHEZI UNIVERSITY
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