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Synthetic method of N-Coumaroyldopamine

A technology of coumaroyl dopamine and a synthesis method, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as being unsuitable for large-scale industrial production of N-coumaroyl dopamine, and achieves The effect of large-scale industrial production, improving yield and reducing by-products

Inactive Publication Date: 2013-04-17
SUZHOU UUGENE BIOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, described preparation method is not suitable for large-scale industrial production N-coumaroyl dopamine

Method used

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  • Synthetic method of N-Coumaroyldopamine
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  • Synthetic method of N-Coumaroyldopamine

Examples

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Embodiment 1

[0043] To protect the phenolic hydroxyl group of dopamine: at room temperature, add 5.0 g of dopamine and 5.6 g of imidazole into a three-neck reaction flask and dissolve them in 50 mL of dichloromethane to form a solution, stir until the raw materials are completely dissolved, lower the temperature of the solution to 0 ° C, and add 10.3 g of t- Butyl dimethyl chlorosilane was added to the solution in batches, and the solution was warmed to room temperature, stirred for 2 hours, and the reaction was monitored by thin-layer chromatography. The solution was first washed twice with 10 mL of water, and then washed once with 10 mL of saturated saline. The organic phase was dried with anhydrous sodium sulfate and concentrated to obtain 12.2 g of dopamine protected by phenolic hydroxyl group;

[0044] Synthesis of N-coumaryl dopamine protected by phenolic hydroxyl group: 5.2g of 4-hydroxycinnamic acid and 6.1g of N,N-diisopropylcarbodiimide were dissolved in 50mL of dichloromethane in...

Embodiment 2

[0047] To protect the phenolic hydroxyl group of dopamine: at room temperature, add 7.0g of dopamine and 8.7g of pyridine into a three-necked reaction flask and dissolve them in 90mL of chloroform to form a solution. -(Trimethylsilyl)ethoxymethyl chloride was added to the solution in batches, and the solution was warmed to room temperature, stirred for 3 hours, and the reaction was monitored by thin-layer chromatography. The solution was first washed twice with 20 mL of water, and then saturated with 20 mL of Wash once with salt water, dry the organic phase with anhydrous sodium sulfate, and concentrate to obtain 17.9 g of dopamine protected by phenolic hydroxyl group;

[0048] Synthesis of N-coumaryl dopamine protected by phenolic hydroxyl group: 8.8g of 4-hydroxycinnamic acid and 8.9g of N,N-diisopropylcarbodiimide were successively dissolved in 100mL of dichloromethane, stirred until the raw materials were completely reacted to obtain a reaction solution, The reaction solut...

Embodiment 3

[0051] Protect the phenolic hydroxyl group of dopamine: at room temperature, add 6.0g of dopamine and 9.9g of triethylamine into a three-necked reaction flask and dissolve in 80mL of 1,2-dichloroethane to form a solution, stir until the raw materials are completely dissolved, and lower the temperature of the solution to 5°C, add 9.4g trimethylchlorosilane to the solution in batches, wait for the solution to rise to room temperature, stir for 2.5 hours, monitor the complete reaction by thin-layer chromatography, wash the solution twice with 18mL of water, and then saturate it with 18mL Wash once with salt water, dry the organic phase with anhydrous sodium sulfate, and concentrate to obtain 14.7 g of dopamine protected by phenolic hydroxyl group;

[0052] Synthesis of N-coumaryl dopamine protected by phenolic hydroxyl group: 5.5g of 4-hydroxycinnamic acid and 8.5g of N,N-diisopropylcarbodiimide were dissolved in 70mL of dichloromethane in sequence, and stirred until the raw mater...

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Abstract

The invention provides a synthetic method of N-Coumaroyldopamine, which belongs to the technical field of medicine synthesis, and solves the problems in the prior art that the synthesized N-Coumaroyldopamine product is low in yield, column chromatographic purification is required, and the prior art is not suitable for large-scale industrial production. The synthetic method comprises the following steps: (1) protecting phenolic hydroxyl group of dopamine: enabling the protecting group and the phenolic hydroxyl group of the dopamine to achieve condensation reaction; (2) synthesizing the N-Coumaroyldopamine with protected phenolic hydroxyl group: enabling 4-hydroxy cinnamic acid to be self-condensed under the action of a dehydrating agent and then continue to react with the dopamine with protected phenolic hydroxyl group; and (3) removing the protecting group: enabling the N-Coumaroyldopamine with protected phenolic hydroxyl group to react with alkali so as to remove the protecting agent on the N-Coumaroyldopamine with protected phenolic hydroxyl group. By adopting the synthetic method provided by the invention, reaction by-products are less, and the end product is high in yield and purity. The synthetic method is simple and convenient to operate and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method of N-coumaryl dopamine, which belongs to the technical field of medicine synthesis. Background technique [0002] N-Coumaroyldopamine (N-Coumaroyldopamine), also known as N-P-Coumaroyldopamine (N-P-Coumaroyldopamine), CAS registration number: 103188-46-1. Its chemical name is N-(3,4-dihydroxyphenylethyl)-3-(4-hydroxyphenyl)acrylamide ((2E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3 -(4-hydroxyphenyl)prop-2-enamide). The structural formula of this N-coumaryl dopamine is as follows: [0003] [0004] N-coumaryl dopamine has an inhibitory effect on the synthesis of prostaglandins and leukotrienes in vitro, so it has been extensively studied. Wherein Chen-Fang Tseng, Satoshi Iwakami, Akihiro Mikajiri etc. are in (Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-β-phenylamine and N-Acyldopamine Derivatives, Chem.Pharm.Bull,40(2)396-400(1992 )) introduces a preparation method of N-couma...

Claims

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Application Information

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IPC IPC(8): C07C235/32C07C231/12
CPCY02P20/55
Inventor 李志强王伸勇王晓俊胡隽恺
Owner SUZHOU UUGENE BIOPHARMA
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