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Preparation method of N-ethyl-D-glucosamine

A technology of glucosamine and glucose, which is applied in the field of preparation of carbohydrate derivatives, can solve the problems of low quality and high impurity content of the product, achieve high yield, better reaction conditions, and overcome the effect of low product purity

Inactive Publication Date: 2020-05-05
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The disadvantage of the above two methods is that the obtained product has high impurity content, which needs to be removed after multiple recrystallizations, and the melting point of the product obtained after separation is only 132-134°C, the optical rotation is -15.4 degrees, and the overall quality is low

Method used

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  • Preparation method of N-ethyl-D-glucosamine
  • Preparation method of N-ethyl-D-glucosamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Put 250g of methanol into the hydrogenation kettle, add 50g of glucose (0.278mol), add 50g of monoethylamine (1.11mol) under stirring, keep at 25-35°C for 30 minutes; add 2.5g of AlNiFe ternary powder catalyst, seal , the system was replaced with nitrogen, the hydrogen pressure was kept at 1.0-2.0 MPa, the system temperature was at 60-80°C, and the reaction was stirred for 12 hours. Cool, release the pressure, remove the catalyst by filtration, freeze the filtrate under stirring, crystallize, filter, and dry the solid to obtain 55 g of N-ethyl-D-glucosamine with a yield of 94.73%. The titer content is 99.8%.

[0030] The reaction process of this embodiment can be by figure 1 expression of the reaction equation.

[0031] figure 2 It is the infrared spectrogram of the product of this example (entrusted to the Department of Materials and Chemistry of Soochow University to test and analyze).

Embodiment 2

[0033] Put methanol 1000g into the hydrogenation kettle, add glucose 180g (1mol), add 180g (4mol) of monoethylamine under stirring, keep at 25-35°C for 30 minutes; add 9g of AlNiFe ternary powder catalyst, airtight, system nitrogen Replacement, keep the hydrogen pressure at 1.0~2.0MPa, the system temperature at 60~80°C, and stir for 12 hours. Cool, release the pressure, remove the catalyst by filtration, freeze the filtrate under stirring, crystallize, filter, and dry the solid to obtain 200 g of N-ethyl-D-glucosamine with a yield of 95.69%. The titer content is 99.6%.

Embodiment 3

[0035] Put 1000g of ethanol into the hydrogenation kettle, add 180g (1mol) of glucose, and pass 180g (4mol) of monoethylamine under stirring, keep at 25-35°C for 30 minutes; add 9g of AlNiFe ternary powder catalyst, airtight, system nitrogen Replacement, keep the hydrogen pressure at 1.0~2.0MPa, the system temperature at 60~80°C, and stir for 12 hours. Cool, release the pressure, remove the catalyst by filtration, freeze the filtrate under stirring, crystallize, filter, and dry the solid to obtain 195 g of N-ethyl-D-glucosamine, with a yield of 93.3%. The titer content is 99.6%.

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Abstract

The invention discloses a preparation method of N-ethyl-D-glucosamine. The method is characterized by sequentially comprising the following steps: (1) dissolving glucose in an alcohol solvent according to a mass ratio of glucose to the alcohol solvent to monoethylamine of 1: (2-10): (1-1.1), introducing monoethylamine gas, performing heating to 35-55 DEG C under a stirring condition, and keeping the temperature for 0.5-1 hour; (2) adding a nickel-containing ternary powder catalyst into the reaction system in the step (1) according to a mass ratio of glucose to the nickel-containing ternary catalyst of 1: (0.02-0.1), introducing hydrogen after the system is subjected to nitrogen conversion, and reacting for 12 hours at the temperature of 50-100 DEG C under the pressure of 0.5-3.0 Mpa; and (3) after the reaction is completed, relieving pressure, carrying out filtering and recovering the catalyst, and performing after-treatment on the filtrate to obtain N-ethyl-D-glucosamine. The obtainedproduct is high in purity and high in yield, and the production cost is reduced. The difficulties of low product purity and repeated recrystallization in the original process are overcome.

Description

technical field [0001] The invention relates to a preparation method of carbohydrate derivatives, in particular to a preparation method of N-ethyl-D-glucosamine which can be used as a drug synthesis intermediate. Background technique [0002] N-Ethyl-D-glucamine (N-Ethyl-D-glucamine), also known as ethylglucamine, is a white crystalline powder with a melting point of 136-142°C. The structural formula is as follows: [0003] . [0004] N-Ethyl-D-glucosamine is an important drug synthesis intermediate, which can be used in drug synthesis and resolution of chiral drugs and intermediates, and can also form salts or complexes with certain drugs, thereby improving the efficacy of drugs. Fat-soluble, so that it can exert the greatest pharmacological effect, such as cyclic adenosine monophosphate and so on. [0005] In the prior art, the main preparation methods are as follows: [0006] One method is the method disclosed in the US patent application US4246193A, which is obtain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/00C07C215/10C07C213/10
CPCC07C213/00C07C213/10C07C215/10
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM