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Method for synthesizing N- (2-hydroxyethyl)-glucosamine

A synthesis method, glucosamine technology, applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as inability to obtain products, achieve high conversion rate, mild reaction conditions, and easy reaction

Inactive Publication Date: 2005-05-04
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After a large number of experiments, it has been proved that the method for preparing N-(butyl)-glucosamine according to EP0477160 to prepare its homologue N-(2-hydroxyethyl)-glucosamine cannot obtain the desired product

Method used

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  • Method for synthesizing N- (2-hydroxyethyl)-glucosamine

Examples

Experimental program
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Effect test

Embodiment 1

[0015] A. Feeding: In a 20L autoclave, add 2kg (10.1mol) of D-glucose, 650g (10.7mol) of ethanolamine, and then add 18L of 90% methanol (10% water content) solvent. After replacing with nitrogen, add 5% Pd-CaCO 3 - 60g of 2% Pb catalyst, blow in high-purity hydrogen, keep the hydrogen pressure at 2-3Mpa, and slowly raise the temperature to 35°C for reaction.

[0016] B. Reaction: Control the reaction temperature to 35-45° C. and the hydrogen pressure to 2-4 MPa to react for 24 hours. The reaction was followed by TLC, and the glucose spot disappeared, and the reaction was terminated.

[0017] C. Post-processing: After the reaction is finished, release the hydrogen pressure and replace with nitrogen. Nitrogen pressure filtration, the filter residue is waste 5% Pd-CaCO 3 -1~5% Pb catalyst, stored in deionized water, recovered after centralized treatment. The light yellow filtrate was put into a 300L glass-lined reaction kettle, and 100L acetonitrile was slowly added under str...

Embodiment 2

[0020] A. Feeding: In a 50L autoclave, add 5kg (25.2mol) of D-glucose, 1.6kg (26.7mol) of ethanolamine, and then add 35L of solvent of 85% isopropanol (15% water content). Add 5% Pd-CaCO after nitrogen replacement 3 - 200g of 4% Pb catalyst, bubbling high-purity hydrogen, keeping the pressure of hydrogen at 2-3Mpa, slowly raising the temperature to 35°C for reaction.

[0021] B. Reaction: Control the reaction temperature to 35-45° C., and the hydrogen pressure to 2-4 MPa to react for 22 hours. The reaction was followed by TLC, and the glucose spot disappeared, and the reaction was terminated.

[0022] C. Post-processing: After the reaction is finished, release the hydrogen pressure and replace with nitrogen. Nitrogen pressure filtration, the filter residue is waste 5% Pd-CaCO 3 -1~5% Pb catalyst, stored in deionized water, recovered after centralized treatment. The light yellow filtrate was put into a 300L glass-lined reaction kettle, and 200L tetrahydrofuran was slowly ad...

Embodiment 3

[0025] A, feed intake: in 400L autoclave, add D-glucose 30kg (151.5mol), ethanolamine 10kg (166.2mol), add the solvent 250L of 80% n-butanol (water content 20%) again. Add 5% Pd-CaCO after nitrogen replacement 3 - 3% Pb catalyst 1.2kg. Bubble high-purity hydrogen, keep the hydrogen pressure at 2-3Mpa, and slowly raise the temperature to 35°C for reaction.

[0026] B. Reaction: Control the reaction temperature to 35-45° C. and the hydrogen pressure to 2-4 MPa to react for 20 hours. The reaction was followed by TLC, and the glucose spot disappeared, and the reaction was terminated.

[0027] C. Post-processing: After the reaction is finished, release the hydrogen pressure and replace with nitrogen. Nitrogen pressure filtration, the filter residue is waste 5% Pd-CaCO 3 -1~5% Pb catalyst, stored in deionized water, recovered after centralized treatment. The light yellow filtrate was put into a 2000L glass-lined reaction kettle, and 1000L acetone was slowly added under strong s...

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Abstract

The invention relates to a kind of method for synthesizing midbody N-(2-ethoxyl)-glucosamine of diabetes therapy medicine miglitol alcohol. The existing literature has no synthesizing method recordation of midbody N-(2-ethoxyl)-glucosamine. The reaction steps of the invention are as follows: A) Stuff casting: in autoclave, add D-glucose and ethanolamine according to molar ratio of D-glucose / ethanolamine with 1 / 1.05-1.10; then add 70-95% alcohols solvent with 5-10 times weight of glucose; and after nitrogen displace, add 5%Pd-CaCO3-1-5%Pb catalyst with 2-10% weight of glucose; inject high purity hydrogen, keep hydrogen pressure to 2-3Mpa, and then intensify the temperature slowly up to reaction temperature; B) Reaction: control reaction temperature in 35-45deg.C, hydrogen pressure in 2-4Mpa, and reaction by 20-24 hours; C) Get white pulverous solid by after-treatment. The invention selects the appropriate catalyst and reasonable hydrogenization technology, so that it can make the reaction condition of glucose and ethanolamine with relatively gentleness, make the reaction easy to proceed, make by-product and other impurity generated badly, and also it has high conversion rate, and more than or equal to 98% purity.

Description

【Technical field】 [0001] The invention relates to a method for synthesizing a drug intermediate, in particular to a method for synthesizing an important intermediate N-(2-hydroxyethyl)-glucosamine of the diabetes treatment drug Miglitol. 【Background technique】 [0002] N-(2-hydroxyethyl)-glucamine is an important intermediate in the synthesis of the diabetes treatment drug Miglitol. Its English name is N-(2-hydroxyethyl)glucamine, and its structural formula is as follows: [0003] [0004] At present, there is no ready-made product for sale of this substance at home and abroad, and the industrialized production of N-(2-hydroxyethyl)-glucosamine is very important for the synthesis of miglitol. US4266025, US4405714 and US2001 / 0019837A1 all mentioned N-(2-hydroxyethyl)-glucosamine, but these three patents all use N-substituted glucosamine as raw material to prepare 1-deoxynojirimycin N-substituted Derivatives, none of them relate to the synthetic method of N-(2-hydroxyethyl...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C215/12
Inventor 陈鹏胡微胡三明
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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