Improved fatty acid monoethanolamide synthesis method

A technology of monoethanolamide and synthesis method, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of toxic products, many impurities and high cost, achieve less side reactions and improve safety factor , the effect of low cost

Active Publication Date: 2017-09-22
上海欧睿生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is: in view of the problems of toxic products, high cost, many impurities and low yield in the synthesis method of fatty acid monoethanolamide in the prior art, it provides a method obtained by using a functionalized resin containing a carboxyl activator. A method for preparing fatty acid monoethanolamide by immobilizing active esters and reacting with ethanolamine to obtain high-quality fatty acid monoethanolamide products in an efficient, fast, safe and clean manner

Method used

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Examples

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Comparison scheme
Effect test

preparation example Construction

[0033] An improved synthetic method of fatty acid monoethanolamide, specifically comprising the following steps: 1) preparation of polystyrene resin (NHS resin) containing N-hydroxysuccinimide: adopting commercially available polystyrene, through organic chemistry general technique Chloromethylation reaction and mercaptomethylation reaction known to personnel to prepare mercaptomethylated polystyrene resin; Styrene resin; or directly buy commercially available mercaptomethyl polystyrene resin; then prepare polystyrene containing N-hydroxysuccinimide by reacting mercaptomethyl polystyrene resin with N-hydroxymaleimide Resin; 2) Preparation of immobilized active ester: step 1) the obtained polystyrene resin (NHS resin) containing N-hydroxysuccinimide and fatty acid carry out condensation reaction in the presence of catalyst EDC / DIC to obtain a reaction product, 3) Preparation of fatty acid monoethanolamide: in the presence of a solvent, react the immobilized active ester with et...

Embodiment 1

[0048] The preparation of embodiment 1 palmitic acid monoethanolamide

[0049] 1) Under nitrogen protection at room temperature, triethylamine (2 ml) was added dropwise to mercaptomethyl resin (2 g, MATRIX-INN), N-hydroxymaleimide (1.1 g, 9.7 mmol) and DMF (40 ml) in the reaction vessel. Stir at room temperature for 24 hours, then continue to stir at 55°C for 4 hours, cool to room temperature, filter to obtain NHS resin, wash with DMF, distilled water and isopropanol twice, and vacuum dry to obtain NHS resin.

[0050] 2) Palmitic acid (1.465 g, 5.72 mmol) and the above NHS resin (1.50 g), DIC (diisopropylcarbodiimide, 0.72 g, 5.72 mmol), triethylamine (2 ml) were suspended in 15 ml di in methyl chloride. The above mixture was stirred at room temperature for 4 hours. Then filter (retain the filtrate, add appropriate amount of palmitic acid, DIC and solvent by HPLC detection, for the next batch of reactions), the collected resin is washed twice with DMF, water, isopropanol an...

Embodiment 2

[0054] Embodiment 2: the preparation of oleic acid monoethanolamide

[0055] 1) Use oleic acid (1.616 g, 5.72 mmol) according to step 2) in Example 1 to obtain immobilized oleic acid active ester with a loading of ~1.0 mmol / g.

[0056] 2) According to step 3) of Example 1 with immobilized oleic acid active ester, 492 mg of oleic acid monoethanolamide (96.3% yield to ethanolamine) was obtained, with a purity of >99.5% (HPLC).

[0057] 3) Return the resin retained in step 2) in this embodiment to step 1) in this embodiment to obtain immobilized oleic acid active ester again, with a loading amount of ~1.0 mmol / g.

[0058] 4) The active ester obtained in step 3) of this example was operated according to step 2) of this example to obtain 486 mg of oleic acid monoethanolamide (95.1% yield to ethanolamine), with a purity of >99.5% (HPLC).

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Abstract

The invention relates to an improved fatty acid monoethanolamide synthesis method, which comprises: 1) preparing a polystyrene resin containing a carboxyl activating agent; 2) carrying out a condensation reaction on the polystyrene resin obtained in the step (1) and fatty acid in the presence of a catalyst to obtain an immobilized active ester; and (3) in the presence of a solvent, carrying out a reaction on the immobilized active ester obtained in the step 2) and ethanolamine, carrying out simple filtration or centrifugation to remove the resin after completing the reaction, carrying out pressure reducing concentration on the obtained liquid phase, and carrying out vacuum drying to obtain the high-quality fatty acid monoethanolamide product. According to the present invention, the condensation reaction is performed under the normal temperature condition, the generation of the by-product is substantially reduced through the selection of the catalyst and the reaction parameters, and the yield of the reaction and the purity of the product are maximized; and with the synthesis method, the defects of more by-products, difficult purification and the like caused by unstable raw material, poor selectivity to ethanolamine and alkali high temperature condition in the prior art are overcome.

Description

technical field [0001] The invention relates to the technical field of synthesis of amide compounds, in particular to a synthesis method of fatty acid monoethanolamide. Background technique [0002] Fatty acid monoethanolamide is an endogenous lipid signaling molecule, a naturally occurring lipid found in many different cells of animal, marine and plant origin. In recent decades, the efficacy of fatty acid monoethanolamides as lipid mediators of endogenous signaling molecules in animal and plant tissues has received increasing attention and attention. Functional fatty acid monoethanolamides mainly include palmitic acid monoethanolamide, oleic acid monoethanolamide, arachidonic acid monoethanolamide and eicosapentaenoic acid monoethanolamide. Palmitic acid monoethanolamide (PEA) is found in soybean oil, peanut oil and egg yolk, and PEA has been confirmed to bind to nuclear receptors in the nucleus (peroxisome proliferator-activated receptor α, PPAR-α), It is also an agonist...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/18C07C233/20C08F8/24C08F8/34C08F8/30C08F8/14C08F8/00
CPCC07C231/02C08F8/00C08F8/14C08F8/24C08F8/30C08F8/34C07C233/18C07C233/20C08F112/08
Inventor 姜苏辛海涛王玉梅
Owner 上海欧睿生物科技有限公司
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