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Novel synthesis technology of tetronic acid

A synthesis process, a technology for quaternary keto acid, applied in the field of brand-new synthesis technology of quaternary keto acid, can solve the problems of dangerous and complicated operation, high cost, long synthesis route, etc., and achieve a shortened reaction route, improved total yield and low cost. Effect

Active Publication Date: 2016-10-12
上海丸全化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the above-mentioned problems such as long synthetic route, dangerous and complicated operation, and high cost caused by using expensive noble metal catalysis in the synthesis, the present invention uses 2-acetoxy acetate as the main raw material to synthesize quaternary ketone acid, this synthesis route is simpler than the method reported in the literature, the raw materials are extremely easy to get, the cost is extremely low, and the yield is high, it has the characteristics of green environmental protection, and is suitable for large-scale industrial production. The synthesis process is as follows:

Method used

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  • Novel synthesis technology of tetronic acid
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  • Novel synthesis technology of tetronic acid

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Embodiment 1

[0020] A kind of brand-new synthetic technique of tetronic acid, specifically comprises the following steps

[0021] (a) Preparation of ethyl 2-acetoxyacetate

[0022] In a reactor equipped with magnetic stirring, at 0°C, dissolve 7.9g of acetyl chloride (0.1mol) in 30ml of tetrahydrofuran, add 10.6g (1.05 eq) of triethylamine, and then slowly add 10.4 g glycolic acid ester (0.1mol), dropwise completed, raised to 10 ℃, stirred for 1h, evaporated part of the solvent under reduced pressure, added an appropriate amount of water, extracted three times with tetrahydrofuran, combined the organic phases and dried, evaporated the organic solvent under reduced pressure to obtain 2-Acetoxyacetate (14.6 g g, 100% yield).

[0023] (b) Preparation of the target product tetronic acid

[0024] Dissolve the above 14.6g of 2-acetoxyacetate and 16.2g of potassium tert-butoxide in 146g of tetrahydrofuran, slowly raise the temperature to reflux (50°C), react for 2h, follow the completion of the...

Embodiment 2

[0028] (a) Preparation of ethyl 2-acetoxyacetate

[0029] In a reactor equipped with magnetic stirring, at 0°C, dissolve 12.3g of acetyl bromide (0.1mol) in 30ml of methyl tert-butyl ether, add 34.8g (1.05 eq) of triethylamine, and then Slowly add 10.4g of glycolic acid ester (0.1mol) dropwise under low temperature. After the dropwise addition, raise to 30°C, stir for 1h, evaporate part of the solvent under reduced pressure, add an appropriate amount of water, extract three times with tetrahydrofuran, combine the organic phases and dry them under reduced pressure. The organic solvent was evaporated to give 2-acetoxyacetate (14.6 g g, 100% yield).

[0030] (b) Preparation of the target product tetronic acid

[0031] Dissolve the above 14.6g of 2-acetoxy acetate and 48.6g of potassium tert-butoxide in 292g of methyl tert-butyl ether, slowly raise the temperature to reflux state (150°C), react for 12h, follow the complete reaction by HPLC, filter, The organic phase was discarde...

Embodiment 3

[0035] (a) Preparation of ethyl 2-acetoxyacetate

[0036] In a reactor equipped with magnetic stirring, at 0°C, dissolve 12.3g of acetyl bromide (0.1mol) in 30ml of tetrahydrofuran, add 23.2g (1.05 eq) of triethylamine, and then slowly add 10.4 g glycolic acid ester (0.1mol), dropwise completed, raised to 15 ℃, stirred for 1h, evaporated part of the solvent under reduced pressure, added an appropriate amount of water, extracted three times with tetrahydrofuran, combined the organic phases and dried, evaporated the organic solvent under reduced pressure to obtain 2-Acetoxyacetate. (14.6 g g, 100% yield).

[0037] (b) Preparation of the target product tetronic acid

[0038] Dissolve the above 14.6g of 2-acetoxyacetate and 32.4g of potassium tert-butoxide in 438g of tetrahydrofuran, slowly raise the temperature to reflux (75°C), react for 5h, follow the completion of the reaction by HPLC, filter, discard the organic phase, The obtained solid was washed three times with tetrahy...

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Abstract

The invention provides a novel synthesis technology of tetronic acid. According to the technology, cheap glycollic acid ester easy to obtain is adopted as an initial precursor and reacts with acetyl halides, a key intermediate 2-acetoxyl acetate is obtained, then, dickman condensation is perfomed on the alkaline condition, and the target product tetronic acid is obtained. The raw materials are easy to obtain, reaction conditions are mild, operation is easy and convenient, the synthesis cost is low, and large-scale industrial production is convenient. The final product tetronic acid is high in purity and yield, and the yield can reach 93% or above.

Description

technical field [0001] The invention belongs to the fields of organic chemistry and medicinal chemistry, and specifically relates to a novel synthesis process of tetronic acid. Background technique [0002] Tetronic acid, also known as tetronic acid, has a chemical formula as shown in formula 1. Its derivatives have many types and large quantities, and are widely distributed in nature. Many natural compounds, such as vitamin C and penicillic acid, are tetronic acid derivatives. . In addition, tetronic acid derivatives have biological activities such as antibacterial, anticoagulant, antiviral and inhibition of HIV protease. In recent years, the research on functional quaternary acid compounds has involved many fields such as medicine, flavors and fragrances, daily chemical materials, organic conductors and superconducting materials, solar energy storage materials, and the synthesis of natural compounds. So tetronic acid is a widely used intermediate in organic synthesis. ...

Claims

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Application Information

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IPC IPC(8): C07D307/60
CPCC07D307/60
Inventor 不公告发明人
Owner 上海丸全化学科技有限公司
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