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Preparation method of voglibose impurity vinyl voglibose

A technology for voglibose and preparation process, which is applied in the preparation of organic compounds, preparation of aminohydroxy compounds, chemical instruments and methods, etc., can solve the problems of no hydrogen spectrum and mass spectrometry, defective preparation process, unreliable data, etc. , to achieve the effect of convenient operation, simple post-processing and simple process

Inactive Publication Date: 2018-07-13
SHANDONG XINHUA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that this process has used DMF, which has a higher boiling point and is difficult to concentrate completely, as a solvent, and simultaneously used the more toxic toluene as the azeotropic solvent, and simultaneously used the more toxic sodium cyanoborohydride as the reducing agent. Expensive Dowex resin, then post-treated with other unconventional ion exchange resins, can be seen at high cost
[0005] At the same time, there are only carbon spectra in the data provided, but no key hydrogen spectra and mass spectra, which shows that its data is unreliable, and further shows that its preparation process is flawed

Method used

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  • Preparation method of voglibose impurity vinyl voglibose
  • Preparation method of voglibose impurity vinyl voglibose
  • Preparation method of voglibose impurity vinyl voglibose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 2.63g (0.015mol) of enamine to a 100ml single-necked flask, then add 1.62g (0.018mol) of 1,3-dihydroxyacetone, then add 40ml of acetone, stir well and then add 0.79g (0.021mol) Sodium borohydride, the reaction was stirred overnight at room temperature. Use concentrated hydrochloric acid to adjust PH=7, after concentrating acetone, add 50ml of water to dissolve the residue, add the mother liquor to 200ml of 732 resin, stir and absorb for half an hour, then put it on the chromatographic column to let off the water, then rinse the resin with 100ml of water, and then Add 100ml of 25-28% concentrated ammonia water to the resin, absorb for 1 hour, and release concentrated ammonia water. The concentrated ammonia water was concentrated to obtain 3.53 g of crude vinyl voglibose with a content of 79.56% and a yield of 75.11%.

Embodiment 2

[0031] Add 1.75g ​​(0.01mol) of enamine to a 100ml single-necked flask, then add 1.35g (0.015mol) of 1,3-dihydroxyacetone, then add 40ml of tetrahydrofuran, stir well and then add 15ml of 1M (0.015mol) Borane tetrahydrofuran complex, stirred overnight at room temperature. Use concentrated hydrochloric acid to adjust PH=7, concentrate THF, then add 50ml of water to dissolve the residue, add the mother liquor to 150ml of 732 resin for half an hour, then put it on the column to let off the water, then rinse the resin with 100ml of water, and then add 80ml Add 25-28% concentrated ammonia water to the resin, absorb it for 1 hour, and release concentrated ammonia water. The concentrated ammonia water was concentrated to obtain 2.56 g of the crude product of vinyl voglibose with a content of 89.88% and a yield of 92.31%.

[0032] Add the obtained crude product into 20ml of absolute ethanol, raise the temperature to reflux, heat filter after complete dissolution, cool the filtrate in...

Embodiment 3

[0034] Add 1.40g (0.008mol) of enamine to a 100ml single-necked flask, then add 1.30g (0.014mol) of 1,3-dihydroxyacetone, then add 40ml of acetonitrile, stir well and then add 1.95g (0.016mol) Sodium triethylborohydride, stirred overnight at room temperature. Use concentrated hydrochloric acid to adjust PH=7, concentrate acetonitrile, then add 50ml of water to dissolve the residue, add the mother liquor to 120ml of 732 resin for half an hour, then put it on the column to let off the water, then rinse the resin with 80ml of water, and then add 70ml of 25 Add ~28% concentrated ammonia water to the resin, absorb it for 1 hour, and release concentrated ammonia water. The concentrated ammonia water was concentrated to obtain 1.96 g of crude vinyl voglibose with a content of 82.75% and a yield of 81.34%.

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Abstract

The invention relates to a preparation method of voglibose impurity vinyl voglibose. According to the preparation method, valienamine and 1,3-dihydroxy acetone are adopted, one kettle method is adopted to prepare vinyl voglibose through reduction using a reducing agent. The preparation method is simple; operation is convenient; subsequent process is simple; technology advantages are obvious; and purity and yield are high.

Description

technical field [0001] The invention relates to a preparation process of voglibose impurity vinyl voglibose, which belongs to the technical field of medicine synthesis. Background technique [0002] Voglibose is used to improve postprandial hyperglycemia in diabetes. This product is only suitable for patients who receive diet therapy and exercise therapy without significant results, or patients who take oral hypoglycemic drugs or insulin preparations in addition to diet therapy and exercise therapy without when significant results are obtained. [0003] Voglibose has a remarkable hypoglycemic effect, and its market share in hypoglycemic drugs is getting higher and higher. It is necessary to study voglibose-related impurities during drug declaration to determine its effect on voglibose in vivo. activity, so the study of voglibose impurities is very necessary. [0004] Literature By Horii, Satoshi et al. Synthesis and α‐D‐glucosidase inhibitory activity of N‐substituted vali...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C213/10C07C215/44
CPCC07C213/08C07C213/10C07C215/44
Inventor 张富强常森
Owner SHANDONG XINHUA PHARMA CO LTD
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