Method for preparing 4-propargyl nitrogen heterocyclic butyl-2-one and 4-allenyl nitrogen heterocyclic butyl-2-one

A technology of azetidine and propargyl nitrogen, applied in the field of preparing 4-propargyl azetidin-2-one and 4-alkenyl azetidin-2-one, which can solve unfavorable industrialization , complex operation and other issues, to achieve the effect of simple route, cheap and easy-to-obtain raw materials, and easy operation

Inactive Publication Date: 2009-06-17
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Since the above method has the disadvantages of complex operation and unfavorable in

Method used

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  • Method for preparing 4-propargyl nitrogen heterocyclic butyl-2-one and 4-allenyl nitrogen heterocyclic butyl-2-one
  • Method for preparing 4-propargyl nitrogen heterocyclic butyl-2-one and 4-allenyl nitrogen heterocyclic butyl-2-one
  • Method for preparing 4-propargyl nitrogen heterocyclic butyl-2-one and 4-allenyl nitrogen heterocyclic butyl-2-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 (3S, 4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(2-propargyl)azetidin-2-one and (3S,4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(1,2-alkenyl)azetidin-2-one Synthesis

[0029] (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl-4-acetylazetidin-2-one (115mg, 0.4mmol), zinc Powder (52mg, 0.8mmol) and propargyl bromide (1mmol) were added to 3mL tetrahydrofuran, heated, reacted for 6 hours, cooled to room temperature, quenched by adding water (8mL), extracted with ethyl acetate (10mL×2 times). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Post-treatment gave (3S, 4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-( 2-propargyl)azetidin-2-one, 79% yield. and (3S,4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl) -4-(1,2-Allenyl)azetidin-2-one, 2% yield.

Embodiment 2

[0030] Example 2 (3S, 4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(2-propargyl)azetidin-2-one and (3S,4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(1,2-alkenyl)azetidin-2-one Synthesis

[0031] (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl-4-acetylazetidin-2-one (115mg, 0.4mmol), zinc Powder (52mg, 0.8mmol) and propargyl chloride (1mmol) were added to 3mL diethyl ether, reacted at 0°C for 24 hours, raised to room temperature, quenched by adding water (10mL), and extracted with dichloromethane (10mL×2 times). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Post-treatment gave (3S, 4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-( 2-propargyl)azetidin-2-one, 54% yield. and (3S,4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl) -4-(1,2-Allenyl)azetidin-2-one, 2% yield.

Embodiment 3

[0032] Example 3 (3S, 4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(2-propargyl)azetidin-2-one and (3S,4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(1,2-alkenyl)azetidin-2-one Synthesis

[0033](2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl-4-benzoylazetidin-2-one (145mg, 0.4mmol), Ketone powder (51.2 mg, 0.8 mmol) and propargyl fluoride (1 mmol) were added to 3 mL of toluene, heated to reflux, reacted for 6 hours, cooled to room temperature, quenched by adding water (8 mL), extracted with ether (10 mL×2 times ). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Post-processing gave (3S, 4R)-3-((R)-1-(tert-butyldimethylsilyloxy) ethyl)-4 -(2-propargyl)azetidin-2-one, yield 8%. and (3S,4R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl yl)-4-(1,2-alkenyl)azetidin-2-one, 2% yield.

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Abstract

The invention relates to a method for preparing 4-propargyl azetidine-2-ketone and/or 4-dialkenyl azetidine-2-ketone. The method can conveniently and efficiently obtain the 4-propargyl azetidine-2-ketone and/or 4-dialkenyl azetidine-2-ketone by taking simple cheap 4-acyloxy-azetidine-2-ketone and propargyl alogenated compound as starting materials. The method has the advantages of convenience and easy operation.

Description

technical field [0001] The invention relates to a preparation method of 4-propargyl azetidin-2-one and 4-alkenyl 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...

Claims

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Application Information

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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
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