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Chemical synthetic method for pyrrole derivatives

A technology of pyrrole and mixed solution, applied in organic chemistry and other directions, can solve the problems of many by-products, high cost and low yield, and achieve the effects of reducing purification steps, improving yield and reducing by-products

Inactive Publication Date: 2013-05-01
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These synthesis methods that cause Maillard reactions of reducing sugars and amino acids under high temperature and pressure have a lot of by-products, and multiple extractions and multi-step column chromatography purifications are necessary to obtain a small amount of 4-(formyl-5-hydroxymethyl Base-1 hydrogen-pyrrol-1-yl) butyric acid, this method of synthesis through the Maillard reaction under high temperature and pressure has the disadvantages of low yield, low purity, cumbersome and complicated method, and high cost.

Method used

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  • Chemical synthetic method for pyrrole derivatives
  • Chemical synthetic method for pyrrole derivatives
  • Chemical synthetic method for pyrrole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0026] 2. The mixed solution described in step 1 was dehydrated by rotary evaporation under reduced pressure at 50°C to obtain 123.5 mg of brown oil;

[0027] 3. Dissolve the brown oil described in step 2 in pure water and load it on a C18 solid phase extraction column, and use water (eluent A) and acetonitrile (eluent B) as eluents to elute successively , collect the acetonitrile eluted fraction, concentrate and remove the acetonitrile to obtain 29.4mg of light brown oily 4-(formyl-5-hydroxymethyl-1hydro-pyrrol-1-yl)butanoic acid, the yield is about 15%, Through high-performance liquid chromatography analysis, the product purity is 95%.

[0028] Example 2

Embodiment 2

[0030] 2. Freeze-dry and dehydrate the mixed solution described in step 1 at -80°C to obtain 103.9 mg of brown oil;

[0031] 3. Dissolve the brown oil described in step 2 in pure water and load it on a C8 solid phase extraction cartridge, and use water (eluent A) and methanol (eluent B) as eluents to elute successively , collect the eluted part of methanol, concentrate to remove methanol to obtain 28.9mg of light brown oil 4-(formyl-5-hydroxymethyl-1hydro-pyrrol-1-yl)butanoic acid, the yield is about 18.5%, After HPLC analysis, the product purity was 98.5%.

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Abstract

The invention relates to a method for synthesizing 4-(formyl-5-hydroxymethyl-1 hydrogen-pyrrole-1-yl) butyric acid, and belongs to the field of organic synthesis. The conventional 4-(formyl-5-hydroxymethyl-1 hydrogen-pyrrole-1-yl) butyric acid can be synthesized by Maillard reaction of monosaccharide and gamma-aminobutyric acid under high pressure at high temperature, but the deficiencies of low yield, low purity, complex process, higher cost and the like exist. The method comprises the steps as follows: reacting 3-deoxyglucosone with gamma-aminobutyric acid, dehydrating to generate 4-(formyl-5-hydroxymethyl-1 hydrogen-pyrrole-1-yl) butyric acid, and purifying with a solid phase extraction method. The method is simple, the yield is increased, few byproducts are generated, and the purity is high.

Description

technical field [0001] The invention relates to a method for synthesizing 4-(formyl-5-hydroxymethyl-1hydro-pyrrol-1-yl)butanoic acid, which belongs to the field of organic synthesis. Background technique [0002] Modern pharmacological experiments have shown that 4-(formyl-5-hydroxymethyl-1hydro-pyrrol-1-yl)butyric acid can protect the liver (Young-Won Chin etc, Bioorganic & Medicinal Chemistry Letters, vol.13 (1) , 2003, p79-81) and increase peripheral blood flow (Miwa Matsui etc., Natural Medicines, vol.52(3), 1998, p232-235) and other biological activities. [0003] 4-(Formyl-5-hydroxymethyl-1hydro-pyrrol-1-yl)butyric acid can be produced by Maillard reaction of monosaccharide and γ-aminobutyric acid under high temperature and pressure. Roland Tressl and Evelyn Kersten studied this synthesis mechanism (J. Agric. Food Chem. 1993, 41, p2278-2285), under high temperature and pressure (160°C, 1.5h), 4-(formyl-5-hydroxymethyl base-1hydro-pyrrol-1-yl) butyric acid yield is ab...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/333
Inventor 陈放彭彤郭亦然唐琳
Owner SICHUAN UNIV