A simple and efficient method for 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, and high cost, and achieve the effect of wide application prospects and simple and efficient preparation

Inactive Publication Date: 2018-01-12
SHIHEZI UNIVERSITY
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  • 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

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  • A simple and efficient method for preparing efavirenz intermediates
  • A simple and efficient method for preparing efavirenz intermediates
  • A simple and efficient method for preparing efavirenz intermediates

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Experimental program
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Effect test

specific Embodiment 1

[0014]

[0015] 2,2,2-trifluoroacetophenone (0.5mmol), phenylacetylene (1.0mmol), CuI (0.05mmol), K 2 CO 3 (0.1mmol) and THF (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 99%.

specific Embodiment 2

[0016]

[0017] 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

[0018]

[0019] 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 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 95%.

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Abstract

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. The method uses copper as a catalyst and trifluoromethyl ketone and terminal alkyne as raw materials to prepare a series of efavirenz intermediates in high yield. The method is characterized by simple operation without any inert gas protection; low cost and no need to add any ligands. Therefore, this method will have broad application prospects in the synthesis of medicine, pesticides, and organic functional materials.

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

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Application Information

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Patent Type & Authority Patents(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
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