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Method for synthesizing pyrroloquinoline quinone

A technology of pyrroloquinoline quinone and morpholine, which is applied in the field of synthesizing pyrroloquinoline quinone, can solve the problems of difficult raw materials and intermediates, high toxicity, high price, etc., achieve low solubility, increase reaction efficiency, increase reaction speed and Yield effect

Inactive Publication Date: 2018-07-27
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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Problems solved by technology

However, these synthetic methods involve raw materials and intermediates that are not easily available, and use metal-catalyzed organic reactions as the key steps, which are highly toxic and expensive

Method used

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  • Method for synthesizing pyrroloquinoline quinone
  • Method for synthesizing pyrroloquinoline quinone
  • Method for synthesizing pyrroloquinoline quinone

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Embodiment 1

[0041] The method for synthesizing pyrroloquinoline quinone may further comprise the steps:

[0042] 1) Take 116.12g of ethyl pyruvate and 159.81g of bromine water (mass fraction 80%), pass through dry carbon dioxide at 20°C and mix and stir for 2h. The reaction product is extracted with dichloromethane, concentrated and dried under normal pressure to obtain 158.1g of compound 1;

[0043] 2) Take 195g of compound 1 and 69.49g of a saturated aqueous solution of hydroxylamine hydrochloride, mix and stir at 20°C for 10 hours, and extract the reaction product with 5 times the volume of dichloromethane, concentrate and dry under reduced pressure to obtain 181.2g of compound 2;

[0044] 3) Take 210g of compound 2 and 118g of 1,4-cyclohexanedione, add 30mg of morpholine and 60mg of iron dodecacarbonyl as catalysts, and reflux in 500ml of toluene for 4h, and the reaction product is separated and purified by chromatography to obtain 197.2 g Compound 3;

[0045] 4) Take 207g compound ...

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Abstract

The invention relates to a method for synthesizing pyrroloquinoline quinone. By the method, ethyl pyruvate is used as a starting synthesizing raw material to prepare the pyrroloquinoline quinone. In the synthesizing method, a step of synthesizing a compound 4 into a compound 5 is a key step of the synthesizing route, in the key step (5), Lewis acid ionic liquid such as hexafluoroantimonate ionic liquid, hexafluorotitanate ionic liquid and hexafluoroborate ionic liquid is creatively used, the ionic liquid has functions of a reaction medium and a catalyst, and therefore, the reaction speed and yield of the steps can be increased. In addition, [BMIm]SbF6 ionic liquid is used optimally, [BMIm]SbF6 ionic liquid and Sc(OTf)3 can form [Sc(OTf)3-x][SbF6] with high catalytic activity, the reactionefficiency can be greatly improved, the solubility of the obtained reaction product in the [BMIm]SbF6 ionic liquid is low, the reaction product precipitates out easily, and therefore, the reaction yield (which can reach 96%) is improved.

Description

technical field [0001] The invention relates to a method for synthesizing pyrroloquinoline quinone, which belongs to the field of chemical industry. Background technique [0002] Pyrroloquinoline quinine (PQQ), a water-soluble quinone compound, is a coenzyme for glucose dehydrogenase and alcohol dehydrogenase, and is considered a new B vitamin (Nature 2003; 422:832). The molecular weight of PQQ is 330. It was first discovered in microorganisms. Subsequent studies have shown that it also exists in animals and plants. The structural formula is shown in the figure below: [0003] [0004] PQQ has been shown to have important physiological functions, such as maintaining skin health, stimulating nerve growth factors, enhancing immune function, promoting cell growth, anti-oxidation, scavenging free radicals, enhancing bacterial tolerance to extreme environmental conditions, and participating in cell signaling, etc. . In the field of medicine, PQQ has physiological functions s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 马科杨雪鹏叶建斌钟桂芳胡仙妹邵化马歌丽周留柱聂晶晶
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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