Synthetic method of pyrroloquinoline quinone

A technology of pyrroloquinoline quinone and synthesis method, which is applied in chemical recovery, organic chemistry and other directions, can solve the problems of harsh reaction conditions, high price, unclear reaction mechanism, etc., and achieves fast reaction speed, high reaction yield, and reduced risk. Effect

Active Publication Date: 2015-04-29
常熟市信谊化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2005, Kou Hiroya et al. took metal-catalyzed organic reaction as the key step to fully synthesize PQQ, but the total yield was only 4.7%[9], and the metal catalyst was highly toxic and expensive
There are many reaction mechanisms in the biosynthetic pathway of PQQ that are not yet clear, and the reaction conditions are harsh, so the development of chemical synthesis of PQQ is an urgent task

Method used

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  • Synthetic method of pyrroloquinoline quinone
  • Synthetic method of pyrroloquinoline quinone
  • Synthetic method of pyrroloquinoline quinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 2-methoxy-5-nitroaniline hydrochloride was used as raw material, dissolved in water, treated with alkali, and then extracted with ethyl acetate to obtain compound 1

[0053] 20g of 2-methoxy-5-nitroaniline hydrochloride (purity 84.3%) was added to a 500ml beaker, 200ml of water was added and stirred, most of the raw materials were dissolved, and NaOH was added to adjust the pH of the aqueous phase to 8. Extracted three times with ethyl acetate, the organic phase was extracted with saturated NaCl, added anhydrous NaSO4 and dried, filtered and then dried by rotary evaporation to obtain 11.6 g of compound 1 as an orange-red solid, with a yield of 83.7% (TLC:PE / EA=5:1 ).

Embodiment 2～10

[0054] Examples 2-10 Preparation of Heteropolyacid Ionic Liquid Used in Compound 1 Synthesis of Compound 2

Embodiment 2

[0056] Add 1,3-propane sultone (0.05mol, 6.1g) and 50ml ethyl acetate into a 100ml flask, stir and keep it warm in an oil bath at 50°C for 30min. Slowly add N-methylimidazole (0.055mol, 4.5g, 4.4ml) dropwise, and keep the reaction for 24 hours after the dropwise addition. After the reaction was finished, it was cooled, filtered, and the filter cake was washed 3 times with ethyl acetate, and vacuum-dried for 48 hours to obtain 10.6 g of white solid 1-(3-sulfonic acid) propyl-3-methylimidazolium salt (MIMPS). The rate is 95%.

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Abstract

The invention discloses a synthetic method of pyrroloquinoline quinone. The synthetic method comprises the following steps: carrying out alkali treatment on 2-methoxy-5-nitroaniline hydrochloride as a raw material, so as to obtain a compound 1; carrying out formylation on the compound 1 under a catalysis condition of an ionic liquid, so as to obtain a compound 2; adopting sodium borohydride to reduce the compound 2 to obtain a compound 3; carrying out diazotization on the compound 3, and then enabling action between the diazotized compound 3 and HBF4 to obtain a compound 4; enabling reaction of the compound 4 and 2-methylethyl acetoacetate to obtain a compound 5; treating the compound 5 with formic acid to obtain a compound 6; carrying out amid catalysis and exchange with the ionic liquid on the compound 6 to obtain a compound 7; enabling reaction of the compound 7 and 2-oxodimethyl glutaconate to obtain a compound 8; feeding hydrogen chloride to the compound 8 under the action of Cu(OAc)2*2H2O to obtain a compound 9; carrying out basic hydrolysis on the compound 9 to obtain a compound 10. The synthetic method disclosed by the invention is cheap and accessible in raw materials, stable, high in reaction yield, quick in reaction, and easy for product separation, and is environment-friendly as the catalyst can be recycled.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a synthesis method of pyrroloquinoline quinone. Background technique [0002] Pyrroloquinoline quinone (Pyrroloquinoline quinone, PQQ) is a new coenzyme of oxidoreductase discovered in the late 1970s. A third coenzyme was discovered later [1]. In 1979, Durin determined that the coenzyme was PQQ, and then Salisbury et al determined the molecular structure of PQQ [2]. As a biologically active substance with multiple physiological functions, PQQ has great potential in the treatment of diseases such as inflammation, hemolytic anemia, transmission nerve excitation disorder, liver disease and osteoporosis. Currently, PQQ has been classified into B Vitamin C is an essential nutritional factor for the human body [3]. [0003] The molecular structure of PQQ is as follows: [0004] [0005] [Chemical Synthesis of PQQ] [0006] Since the PQQ molecule was identified in 1979, PQQ has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCY02P20/584C07D471/04
Inventor 袁荣鑫付任重柴文陈志凯马运声汪权
Owner 常熟市信谊化工有限公司
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