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Process for synthesizing chlorogenic acid and its derivative

A synthesis method and technology of derivatives, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid esters, etc., can solve the problems of low yield and the inability to apply a large number of derivatives to the synthesis method, and achieve simple operation, Effects with short steps and simple post-processing

Inactive Publication Date: 2008-10-29
ZHEJIANG UNIV
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Problems solved by technology

The obvious shortcoming of this method is the use of an inappropriate quinic acid precursor compound skeleton, resulting in multiple steps requiring the use of hydroxyl protection strategies and subsequent tedious acid-base deprotection operations, while chlorogenic acid It is easily oxidized under aggressive conditions, so the whole process leads to very low yield
[0006] Although the yield of the above-mentioned method has been improved, this synthetic method cannot be applied to the synthesis of a large number of derivatives. Therefore, it is very important to find a high-yield and effective synthetic method for the industrial production of chlorogenic acid and its derivatives and the application in the field of medicine. meaningful work

Method used

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  • Process for synthesizing chlorogenic acid and its derivative
  • Process for synthesizing chlorogenic acid and its derivative
  • Process for synthesizing chlorogenic acid and its derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Example 1 : Synthesis of Compound (1) under Dicyclohexylcarbodiimide Catalyzed Condensation Conditions

[0028] Add 1.2 mmoles of 3,4-diacetoxyphenylacrylic acid, 2 mmoles of dicyclohexylcarbodiimide, and 20 ml of anhydrous dichloromethane into the reaction flask, and stir at room temperature for 20 minutes. After white turbidity appears, Add 1 mmol 3,4-di-oxo-acetonylidene quinic acid, 0.2 mmol 4-dimethylaminopyridine (DMAP), and react the whole solution at room temperature for 12 hours, remove insoluble matter by suction filtration, evaporate the solvent, Precipitate to obtain a white solid, then add 15 ml of tetrahydrofuran, then dropwise add 5 ml of 1N hydrochloric acid, and react at room temperature for 68 hours. It is detected by thin layer chromatography TLC that the ratio of the product to the raw material does not change, and salt is added to the reaction system Saturated, extracted with chloroform (20 ml × 4), the combined chloroform layers were washed with a...

Embodiment 2

[0029] Example 2 : Synthesis of Compound (1) under Methylisobutylcarbodiimide Catalyzed Condensation Conditions

[0030] Add 1.2 mmoles of 3,4-diacetoxyphenylacrylic acid, 2 mmoles of methylisobutylcarbodiimide, and 20 ml of anhydrous dichloromethane into the reaction flask, stir at room temperature for 20 minutes, and white turbidity appears Finally, add 1 mmol 3,4-di-oxo-acetonylidene quinic acid, 0.2 mmol 4-dimethylaminopyridine, and react the whole solution at room temperature for 12 hours, remove insoluble matter by suction filtration, and then add 5 ml of 1N hydrochloric acid, reacted at room temperature for 68 hours, detected by thin-layer chromatography TLC that the ratio of the product and the raw material did not change any more, saturated the reaction system with salt, extracted with chloroform (20 ml × 4), combined the chloroform layers with a large amount of Wash with water, wash with saturated brine, and dry over anhydrous sodium sulfate. Reversed phase silica...

Embodiment 3

[0031] Example 3 : 4-pyrrolidinylpyridine is the synthesis of compound (1) under organic base conditions

[0032] Add 1.2 mmoles of 3,4-diacetoxyphenylacrylic acid, 2 mmoles of dicyclohexylcarbodiimide, and 20 ml of anhydrous dichloromethane into the reaction flask, and stir at room temperature for 20 minutes. After white turbidity appears, Add 1 mmol 3,4-di-oxo-acetonylidene quinic acid, 0.2 mmol 4-pyrrolidinylpyridine (PPY), and react the whole solution at room temperature for 12 hours, remove insoluble matter by suction filtration, and then add 5 One milliliter of 1N hydrochloric acid was reacted at room temperature for 68 hours. It was detected by thin-layer chromatography TLC that the ratio of the product and the raw material did not change any more. The reaction system was saturated with salt, extracted with chloroform (20 ml × 4), and the combined chloroform layers were used Wash with plenty of water, wash with saturated brine, and dry over anhydrous sodium sulfate. ...

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Abstract

The invention provides a synthetic method of chlorogenic acid and derivatives thereof. The method comprises allowing beta-phenylacrylic acid compound and alkylidenedioxy-protected quinic acid compound to react at 0-100 DEC C under stirring in organic solvent in the presence of dicyclohexylcarbodiimide and analog thereof as condensing agent and organic alkali as catalyst for 1-72 hours, and hydrolyzing at 0-100DEC C in diluted acid solution for 1-72 hours. The synthetic method has reasonable design, simple operation, less reaction step, simple post treatment, and high yield compared with conventional acyl chloride method.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for synthesizing chlorogenic acid and derivatives thereof. Background technique [0002] 5-Oxo-phenylacryloylquinic acid compounds are a general term for a class of common natural products with various physiological activities, the most famous of which is chlorogenic acid. Chlorogenic acid (Chlorogenic acid) is a monosubstituted phenolic acid formed by the condensation of caffeic acid and quinic acid (quinic acid, quinic acid). Quinic acid (5-O-caffeoylquinic acid) is a phenylpropanoid compound produced by plants through the shikimic acid pathway during aerobic respiration. Chlorogenic acid is the main active ingredient of antibacterial detoxification, anti-inflammatory and choleretic of many medicinal materials, such as honeysuckle, capillary, Eucommia and Chinese patent medicines, such as Fuganni, Shuanghua injection, acne oral liquid, etc., and it is also the main ac...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/08
Inventor 赵昱周琪于荣敏郝小江胡利红白骅
Owner ZHEJIANG UNIV
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