Method for preparing 4-alkynyl azetidin-2-one

A technology of azetidinine and alkynyl nitrogen, which is applied in the field of preparation of 4-alkynylazetidin-2-one, can solve the problems of complex operation and unfavorable industrialization, and achieve cheap and easy-to-obtain raw materials, simple route, The effect of easy operation

Inactive Publication Date: 2009-06-24
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Since the above method has the disadvantages of complex operation and unfavorable in

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 preparing 4-alkynyl azetidin-2-one
  • Method for preparing 4-alkynyl azetidin-2-one
  • Method for preparing 4-alkynyl azetidin-2-one

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0027] Synthesis of Example 1 (3S, 4S)-3-((R)-1-(tert-butyldimethylsilyloxy) ethyl)-4-phenylethynyl azetidin-2-one

[0028] Zinc trifluoromethanesulfonate (435 mg, 1.2 mmol) was added to 4 mL of toluene, and triethylamine (418 μL, 3.0 mmol) was added, and stirred at 25° C. for 10 minutes. Phenylacetylene (1.2 mmol) was added to the system. Then the mixture was stirred at 40°C for 1 hour, and (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl-4-acetylazetidin-2 was added - Ketone (287mg, 1mmol). After reacting for 6 hours, cool to room temperature, add water (8mL) to quench, and extract with ethyl acetate (10mL×2 times). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. After treatment, 240 mg of (3S, 4S)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-phenylethynylazetidin-2-one was obtained, producing The rate is 73%.IR: 3.50, 3087, 2955, 2893, 2857, 1763, 1719, 1338, 1137cm -1 ; 1 H NMR (300MHz, CDCl 3 )δ 7.42-7...

Example Embodiment

[0029] Example 2 Synthesis of (3S, 4S)-3-((R)-1-(tert-butyldimethylsilyloxy) ethyl)-4-phenylethynyl azetidin-2-one

[0030] Zinc chloride (163mg, 1.2mmol) was added to 4mL of benzene, then triethylamine (418μL, 3.0mmol) was added, and stirred at 0°C for 10 minutes. Phenylacetylene (2 mmol) was added to the system. Then the mixture was stirred at 0°C for 1 hour, and (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl-4-acetylazetidin-2 was added - Ketone (1mmol). After reacting for 6 hours, cool to room temperature, add water (8mL) to quench, and extract with ethyl acetate (10mL × 2 times). Combine the organic phases, dry them over anhydrous sodium sulfate and concentrate under reduced pressure. Aftertreatment Obtained (3S, 4S)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-phenylethynylazetidin-2-one 160mg, the yield was 48%.

Example Embodiment

[0031] Example 3 Synthesis of (3S, 4S)-3-((R)-1-(tert-butyldimethylsilyloxy) ethyl)-4-phenylethynyl azetidin-2-one

[0032]Zinc bromide (450mg, 2mmol) was added to 4mL of tetrahydrofuran, and then pyridine (2.0mmol) was added, and stirred at 65°C for 10 minutes. Phenylacetylene (1 mmol) was added to the system. Then the mixture was stirred at 65°C for 2 hours, and (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl-4-acetylazetidin-2 was added - Ketone (1.2mmol). After reacting for 6 hours, cool to room temperature, add water (8mL) to quench, and extract with ethyl acetate (10mL × 2 times). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. After Treatment afforded (3S,4S)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-phenylethynylazetidin-2-one 100 mg, yield 30%.

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 preparing 4-alkynyl-2-azetidinone. Simple and cheap 4-acyloxy-2-azetidinone and alkyne are used as raw materials for preparing the 4-alkynyl-2-azetidinone conveniently and efficiently. The method has the advantages of simplicity and easy operation and is applied to industrialized production.

Description

technical field [0001] The invention relates to a preparation method of 4-alkynyl azetidin-2-one. Background technique [0002] More than 100 years ago, a large number of people died of infectious diseases and wound bacterial infections, because at that time people did not find drugs that could inhibit those infectious bacteria. When the miraculous nature produced these microorganisms, it also secretly prepared weapons against them, waiting for human beings to discover them. Interestingly, these are derived from themselves, which are antibiotics, a class of low-molecular-weight microbial metabolites that can inhibit the growth of other microorganisms at low concentrations. [0003] However, the development of antibiotics was quite slow before the 1940s, and the available drugs were very limited, until the emergence of penicillin (β-lactam antibiotics) opened the curtain of antibiotic research. First, Fleming discovered penicillin in 1929, and then, through the joint effort...

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): C07D205/08
Inventor 姜标田华赵小龙王万军
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap