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Preparation method of p-nitrobenzyl 2-diazoacetoacetate

A technology of diazoacetate and p-nitrobenzyl ester, applied in directions such as organic chemistry, can solve the problems of complex process route, difficult availability of diazonium reagents, expensive catalysts, etc., and achieves easy industrial production, high yield, simplification and the like. The effect of the process operation steps

Active Publication Date: 2011-03-09
江西如益科技发展有限公司
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Problems solved by technology

[0007] The disadvantage of the first route is: 2-diazoacetoacetic acid needs to be synthesized by itself, the process route is complex and the catalyst is relatively expensive, and the yield is 92.0%.
[0008] The shortcoming of the second route is: the total yield is only 69.2%, and the yield of the process transesterification product (III) is low, and the diazotization reagent TsN 3 Not easy to get

Method used

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  • Preparation method of p-nitrobenzyl 2-diazoacetoacetate

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Embodiment 1

[0018] Embodiment 1, the preparation of p-nitrobenzyl acetoacetate i.e. compound (III):

[0019] Add 43.5g of p-nitrobenzyl alcohol and 150g of toluene to the flask, then add 45.9g of 2.2-dimethyl-1.3-oxcyclohex-4-en-6-one, then raise the temperature and stir the reaction at 30-35°C for 5.0h HPLC tracking reaction Finish, cool down 20~25 ℃ for later use.

Embodiment 2

[0020] Embodiment 2, the preparation of 2-diazoacetoacetic acid p-nitrobenzyl ester compound (VI):

[0021] In another flask, add 9.0 g of sodium bicarbonate, 23.0 g of sodium azide, 2.0 g of phase transfer catalyst tri-n-butyl methyl ammonium chloride, and 160 g of purified water, start stirring, raise the temperature to 20-30°C, and start adding formazan Sulfonyl chloride 38.0g, temperature control at 20-30°C for about 40 minutes to complete the dropwise addition, start dropwise adding the standby solution after the reaction in Example 1, temperature control at 25-30°C, dropwise for about 1.0h, at 25-30°C Keep warm for 4.0 hours, HPLC detects that the reaction is complete, and then lower the temperature by 0-5°C.

[0022] Insulate for 1.0h, filter, drain, dig out the filter cake, put into another flask, add 200g of water, 200g of toluene, stir to cool down to 0-5°C, continue stirring for 2.0h, filter, drain, dig out the filter cake, at 50-60 After drying under reduced press...

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PUM

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Abstract

The invention provides a preparation method of p-nitrobenzyl 2-diazoacetoacetate, wherein, the p-nitrobenzyl 2-diazoacetoacetate is made by two-step reaction. The preparation method has the advantages of simplified processing steps, easy industrialized production, lowered production cost, improved product quality and higher yield, wherein, by taking nitrobenzyl alcohol as a standard, the total mol yield reaches more than or equal to 95%, and the purity of the product compound (IV) reaches more than or equal to 99.5%.

Description

technical field [0001] The invention relates to a preparation method of p-nitrobenzyl 2-diazoacetoacetate. Background technique [0002] 2-diazoacetoacetate p-nitrobenzyl ester (IV) is the key intermediate of carbapenem compounds such as synthetic imines, and according to literature reports at present, prepares 2-diazoacetoacetate p-nitrobenzyl ester, There are two main synthetic routes: [0003] The first route was published in Chemical Communications 2006 12 13 16-1318: [0004] [0005] The second route is disclosed in GB:2173801: [0006] [0007] The disadvantage of the first route is that 2-diazoacetoacetic acid needs to be synthesized by itself, the process route is complex and the catalyst is relatively expensive, and the yield is 92.0%. [0008] The shortcoming of the second route is: the total yield is only 69.2%, and the yield of the process transesterification product (III) is low, and the diazotization reagent TsN 3 Not easy to get. Contents of the i...

Claims

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Application Information

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IPC IPC(8): C07C245/18
Inventor 刘雨林张涛宋志刚周强仇诗军
Owner 江西如益科技发展有限公司
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