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Method for preparing miglitol intermediate N-hydroxyethyl glucosamine

A technology of glucosamine and miglitol, which is applied in the field of drug synthesis, can solve the problems of many by-products, difficult to purify, complicated steps and the like, and achieves the effects of safe reaction, low cost and simple operation process

Active Publication Date: 2010-11-24
鲁南新时代生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The general chemical synthesis method is cumbersome, with many by-products, and it is difficult to purify by ordinary methods, so now most of them use chemical and biological methods to prepare miglitol

Method used

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  • Method for preparing miglitol intermediate N-hydroxyethyl glucosamine
  • Method for preparing miglitol intermediate N-hydroxyethyl glucosamine
  • Method for preparing miglitol intermediate N-hydroxyethyl glucosamine

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Add 1100ml of anhydrous methanol, 550g of glucose, and 201.5g of ethanolamine into a 5L four-neck flask, add 65g of anhydrous sodium carbonate, heat up to 52°C, react for 1 hour, cool down to 9°C, and slowly add 174.2g of lithium aluminum hydride, After about 5 hours, the reaction was completed, filtered, and 440 ml of ethyl acetate was added to the filtrate for crystallization. After 6 hours, suction filtered and dried to obtain the target product N-hydroxyethylglucamine.

[0030] Dissolve the crude product of N-hydroxyethylglucosamine in 495ml of methanol, add 9.9g of activated carbon, reflux for 1 hour, filter out the activated carbon, cool the filtrate to 12°C, add 396ml of ethyl acetate, crystallize, and suction filter after 7 hours. The filter cake was vacuum-dried for 24 hours (the temperature was 25-45° C., and the vacuum degree was greater than 0.09 MPa), and 661 grams of white N-hydroxyethylglucamine crystals were obtained, with a yield of 96%, a purity of 99% ...

Embodiment 2

[0032] Add 1100ml of absolute ethanol, 550g of glucose, and 205g of ethanolamine into a 5L four-necked bottle, add 97.2g of anhydrous sodium carbonate, heat up to 48°C, react for 0.5 hours, cool down to 8°C, slowly add 232.0g of lithium aluminum hydride, After about 6 hours, the reaction was completed, filtered, and 660 ml of ethyl acetate was added to the filtrate for crystallization. After 6 hours, suction filtered and dried to obtain the target product N-hydroxyethylglucamine.

[0033] Dissolve the crude product of N-hydroxyethylglucosamine in 500ml of methanol, add 50g of activated carbon, reflux for 1 hour, filter out the activated carbon, cool the filtrate to 8°C, add 500ml of ethyl acetate, crystallize, after 5 hours, filter with suction, The filter cake was vacuum-dried for 24 hours (at a temperature of 25-45° C. and a vacuum greater than 0.09 MPa) to obtain 675 grams of white N-hydroxyethylglucosamine crystals, with a yield of 98%, a purity of 99.5% (by HPLC detection)...

Embodiment 3

[0035] Add 825ml of n-propanol, 550g of glucose, and 203.5g of ethanolamine into a 5L four-necked bottle, add 35g of anhydrous calcium oxide, heat up to 51°C, react for 1.5 hours, cool down to 10°C, and slowly add 174.2g of sodium borohydride , about 7 hours, the reaction was completed, filtered, 600ml of ethyl acetate was added to the filtrate, crystallized, and after 8 hours, suction filtered and dried to obtain the target product N-hydroxyethylglucamine.

[0036] Dissolve the crude product of N-hydroxyethylglucosamine in 520ml of methanol, add 20.8g of activated carbon, reflux for 1 hour, filter out the activated carbon, cool the filtrate to 10°C, add 350ml of ethyl acetate, crystallize, after 6 hours, filter with suction, The filter cake was vacuum-dried for 24 hours (the temperature was 25-45° C., and the vacuum degree was greater than 0.09 MPa), and 647 grams of white N-hydroxyethylglucamine crystals were obtained, with a yield of 94%, a purity of 99% (detected by HPLC), ...

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Abstract

The invention relates to a method for preparing miglitol intermediate N-hydroxyethyl glucosamine which is used for curing diabetes mellitus. The method is characterized by comprising the following steps: taking glucose and ethanolamine as raw materials, controlling reaction temperature and reaction environment in the presence of a solvent and a proper amount of dehydrating agent, carrying out a reaction with metal hydride, finishing the reaction, and obtaining white crystals of the droxyethyl glucosamine after aftertreatment and refining. Yield coefficient is more than 95% and purity is more than 99% (HPLC detection).

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of a key intermediate of miglitol, a drug for treating diabetes. Background technique [0002] Miglitol is a new type of hypoglycemic drug researched and developed by the German Bayer Pharmaceutical Company in the early 1980s, and it is a new small intestinal α-glucosidase inhibitor. Also known as Miconidol, chemical name: 1-(2-hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidine triol; boiling point: 246.0°C, melting point: -20.0°C , the structural formula is as follows: [0003] [0004] The structure of Miglitol is similar to that of glucose, and it can reversibly competitively inhibit pseudomonosaccharide α-glucosidase, and it can inhibit α-glucosidases such as sucrase, glucoamylase, maltase, and isomaltase on the brush border of small intestinal villi , trehalase, and lactase all have inhibitory effects. It is an efficient inhibitor of sucrase,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/12C07H1/00
Inventor 赵志全张清德杨勇祥
Owner 鲁南新时代生物技术有限公司
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