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A kind of supported vanadium chiral catalyst for asymmetric synthesis of esomeprazole and preparation method thereof

A technology of chiral catalyst and esomeprazole, which is applied in the field of supported vanadium chiral catalyst and its preparation, can solve the problems of unsuitability for industrial production, complex operation, limited substrate, etc., and achieve easy control of reaction and low price , the effect of short process

Active Publication Date: 2018-11-02
ZHEJIANG SHUREN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of the resolution method is that the highest yield is only 50%. Although higher yields can be achieved through continuous racemization and resolution, the operation is very complicated, and it can be mass-produced in industry but the cost is high
Enzyme kinetic resolution and enzyme-catalyzed asymmetric synthesis are both based on the catalytic performance of enzymes. Due to the strong specificity of enzymes, the applicable substrates are relatively limited and are not suitable for industrial production.

Method used

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  • A kind of supported vanadium chiral catalyst for asymmetric synthesis of esomeprazole and preparation method thereof
  • A kind of supported vanadium chiral catalyst for asymmetric synthesis of esomeprazole and preparation method thereof
  • A kind of supported vanadium chiral catalyst for asymmetric synthesis of esomeprazole and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0044] The production method prepared by the asymmetric oxidation of esomeprazole is carried out in the following steps successively:

[0045] 1), preparation of supported vanadium chiral catalyst (i.e. the supported catalyst for the preparation of esomeprazole)

[0046] Add 450 milliliters of methanol in a 1-liter reaction flask, then add a mixture of 100 grams of silica-loaded chitosan-derived Schiff base 4 and ammonium metavanadate (mass ratio is 60:1), and stir at a temperature of 65°C 5.5 hours, then filter, and wash with methanol three times, put it in a vacuum drying oven at 50°C for 12 hours, the content of vanadium is 1.8% as measured, and set aside;

[0047] 2), the supported catalyst obtained in the above step 1) is activated

[0048]Load the preliminarily prepared supported catalyst into a fixed bed reactor, and activate the catalyst for 2 to 5 hours under nitrogen purging (120-150° C.) until the activation is completed (that is, no liquid flows out from the lower...

Embodiment 2

[0052] The preparation process of esomeprazole is referring to embodiment 1, changes the mass ratio of Schiff base 4 and ammonium metavanadate in step (1), hydrogen peroxide equivalent, cooling temperature and reaction time in step (3), its result is as shown in the table 1 shows:

[0053] Table 1

[0054]

[0055] In conclusion, No. 5 has the best reaction effect. Under this condition, the yield can reach 90.0%, and the ee value is 82.1%. In addition, under this catalytic condition, the number of cycles of the supported vanadium chiral catalyst was considered, and the specific results are shown in Table 2:

[0056] Table 2

[0057] Cycles

[0058] The results show that under the catalytic conditions, the supported vanadium chiral catalyst can be recycled for 5 times, and the catalytic effect does not decrease significantly.

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Abstract

The invention relates to a load-type vanadium chiral catalyst for asymmetric synthesis of esomeprazole and a preparation method thereof. Low-cost chitosan is taken as a raw material; the raw material is loaded onto a silicon dioxide carrier and then reacts with substituted salicylaldehyde so as to acquire schiff base; the schiff base has complex reaction with ammonium metavanadate, so as to acquire the load-type vanadium chiral catalyst; the catalyst is subjected to infrared and thermogravimetric analysis and structural characterization of scanning electron microscope; the weight of vanadium is 0.5-5% of the total weight. The load-type vanadium chiral catalyst can be utilized to continuously prepare esomeprazole. The load-type vanadium chiral catalyst provided by the invention has the advantages of wide raw material source, low cost, mild reaction condition, high yield, suitability for continuous industrial production, high catalyst activity, stability, high dispersity of active components, long service life, reuse, short flow, simplicity in operation, easiness in reaction control, simple requirement for equipment and cost greatly lower than that of the other technique.

Description

technical field [0001] The invention relates to a supported vanadium chiral catalyst for asymmetric synthesis of esomeprazole and a preparation method thereof. Background technique [0002] Esomeprazole, English name Esomeprazole, Chinese alias: 5-methoxy-2-((S)-((4-methoxy-3,5-dimethyl-2-pyridyl)methyl) Sulfuryl)-1H-benzimidazole is the world's first synthetic and clinically used optical isomer proton pump inhibitor (proton pump inhibitor, PPI), which reduces gastric acid by inhibiting the H+ / K+-ATPase of gastric parietal cells secreted to prevent the formation of gastric acid. Esomeprazole is the (S)-type isomer of omeprazole, with little dependence on CYP2C19, high and long-lasting active drug concentration in plasma, little interaction between drugs, bioavailability and blood drug concentration It is higher than omeprazole or (R)-omeprazole, and the half-life is extended to more than 2 hours. Therefore, the drug effect is higher and longer than that of omeprazole, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07D401/12C07B53/00
CPCB01J31/2217B01J2231/70B01J2531/0244B01J2531/56C07B53/00C07B2200/07C07D401/12
Inventor 沈超金建忠孙娜波赵林伟章鹏飞
Owner ZHEJIANG SHUREN UNIV
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