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
View PDF3 Cites 2 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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
Comparison scheme
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), ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap