Synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine

A technology of methacryloyloxyethylphosphorylcholine and synthesis method, which is applied in the field of synthesis of 2-methacryloyloxyethylphosphorylcholine, the main component of artificial cell membranes, and can solve the problem of being unable to provide long-term stable products Problems such as supply, long synthetic route, cumbersome operation, etc., achieve the effect of reducing the types of reaction raw materials, low price, and simplifying the synthetic route

Active Publication Date: 2017-08-18
李铁龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, no company in China can carry out large-scale industrialization of this product, and its synthesis scale generally only reaches the gram level, which is only suitable for research and cannot provide long-term stable commodity supply.
[0006] There are many problems in the existing synthetic route. The synthetic route is long and requires four-step reactions, and each step requires post-processing, which makes the operation cumbersome; high-precision reaction equipment is required, and a high-pressure and high-vacuum resistant reactor is required to complete the reaction. ; The reaction often encounters unpredictable sudden polymerization and the reaction fails; toxic and harmful solvents and reagents are used, including toluene and phosphorus trichloride

Method used

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  • Synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine
  • Synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine
  • Synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine

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Embodiment 1

[0029] A method for synthesizing 2-methacryloyloxyethyl phosphorylcholine, the main component of an artificial cell membrane, comprising the steps of:

[0030] Step 1) In a 500 ml round bottom flask, dissolve 15.3 g of phosphorus oxychloride in 300 ml of dry acetonitrile, and lower the temperature of the reaction solution to -5°C. Then 10.1 g of triethylamine was added to the reaction system. Add 29 grams of 2,3-dibromo-2-methylpropionate hydroxyethyl ester dropwise, keeping the temperature below 0°C during the dropwise addition. After the dropwise addition, the mixture was stirred at 0° C. for 2 hours, slowly raised to room temperature, and stirred for another half an hour. Then the reaction solution was cooled to 0°C, 10.1 g of triethylamine was added, and 14 g of choline chloride was added in batches. The mixture was slowly raised to room temperature and stirred for 2 hours. TLC traced the disappearance of the starting material. The reaction liquid was cooled to 0° C. ag...

Embodiment 2

[0037] A method for synthesizing 2-methacryloyloxyethyl phosphorylcholine, the main component of an artificial cell membrane, comprising the steps of:

[0038] Step 1) In a 500 ml round bottom flask, dissolve 15.3 g of phosphorus oxychloride in 300 ml of dry acetonitrile, and lower the temperature of the reaction solution to -5°C. Then 10.1 g of triethylamine was added to the reaction system. Add 32 grams of 2,3-dibromo-2-methylpropionate hydroxyethyl ester dropwise, keeping the temperature below 0°C during the dropwise addition. After the dropwise addition, the mixture was stirred at 0° C. for 2 hours, slowly raised to room temperature, and stirred for another half an hour. Then the reaction solution was cooled to 0°C, 10.1 g of triethylamine was added, and 14 g of choline chloride was added in batches. The mixture was slowly raised to room temperature and stirred for 2 hours. TLC traced the disappearance of the starting material. The reaction liquid was cooled to 0° C. ag...

Embodiment 3

[0041] A method for synthesizing 2-methacryloyloxyethyl phosphorylcholine, the main component of an artificial cell membrane, comprising the steps of:

[0042]Step 1) In a 500 ml round bottom flask, dissolve 15.3 g of phosphorus oxychloride in 300 ml of dry acetonitrile, and lower the temperature of the reaction solution to -5°C. Then 10.1 g of triethylamine was added to the reaction system. Add 29 grams of 2,3-dibromo-2-methylpropionate hydroxyethyl ester dropwise, keeping the temperature below 0°C during the dropwise addition. After the dropwise addition, the mixture was stirred at 0° C. for 2 hours, slowly raised to room temperature, and stirred for another half an hour. Then the reaction solution was cooled to 0°C, 10.1 g of triethylamine was added, and 15 g of choline chloride was added in batches. The mixture was slowly raised to room temperature and stirred for 2 hours. TLC traced the disappearance of the starting material. The reaction liquid was cooled to 0° C. aga...

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Abstract

The invention provides a synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine. The synthetic method comprises the following steps: (1) dissolving phosphorus oxychloride in acetonitrile, adding triethylamine at 0 to 10 DEG C, dropwise adding 2,3-dibromo-2-hydroxyethyl methacrylate, reacting at -10 to 0 DEG C, adding triethylamine and choline chloride to facilitate the reaction at -10 to 0 DEG C, and obtaining bromophosphorylcholine after the reaction is ended; and (2) dissolving the bromophosphorylcholine obtained in the step (1) in ethanol, adding zinc powder, severely stirring, and obtaining 2-methacryloyloxyethyl phosphorylcholine. By adopting the synthetic method, a synthetic route of the original 2-methacryloyloxyethyl phosphorylcholine is simplified, no treatment is needed after the purification during the synthetic route, and the next operation can be directly carried out; severe conditions in the synthetic route are avoided, high-end equipment is not needed, uncontrollable factors during the synthetic route are reduced; raw materials are easy to obtain, the price is low, the cost is reduced, the use of solvents and raw materials with large toxicity is avoided, and the green synthesis is realized; and a foundation is set for the industrialization of the 2-methacryloyloxyethyl phosphorylcholine.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method for synthesizing 2-methacryloyloxyethylphosphorylcholine, the main component of artificial cell membranes. Background technique [0002] At the end of the 20th century, NOF CORPORATION. was at the forefront of the world in the development of a series of biomimetic materials. The medical biomimetic materials they developed are due to their extremely high moisture-retaining and breathable properties and their excellent compatibility with human cell membranes. Similar ingredients and characteristics, known as artificial cell membrane. [0003] This high-end medical bionic material has a high degree of biocompatibility, and is mainly used in the fields of biomedicine and medical devices, and has been commercialized in the following fields: used to manufacture hemodialysis membranes to treat uremia patients; coated on biological scaffolds (scaffold) The material i...

Claims

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Application Information

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IPC IPC(8): C07F9/10
CPCC07F9/10
Inventor 李铁龙谢同张彤
Owner 李铁龙
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