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Novel preparation of sofalcone

A sofa ketone and a novel technology, applied in the field of sofa ketone preparation, can solve problems such as low yield and poor quality of intermediates, and achieve the effects of improving yield, ensuring quality and simplifying processing methods

Inactive Publication Date: 2009-05-20
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] c. Several steps of reaction intermediates in literature method have low yield and poor quality
[0018] Although some other relevant literatures have made some adjustments to the traditional process in many aspects such as catalysts and reaction conditions, they have not fundamentally solved the problem.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of 1-[2-hydroxyl-4-(3-methyl-2-butenyloxy)-phenyl]-3-(4-hydroxyphenyl)-propenone (IV)

[0038] In a 3000mL reaction flask equipped with stirring, condenser, thermometer and dropping funnel, add 200g of 2-hydroxy-4-(3-methyl-2-butenyloxy)acetophenone and 750mL of absolute ethanol, start stirring , Add 1250 mL of 10% potassium hydroxide aqueous solution. After the reaction system was dissolved, slowly add 27.7g p-hydroxybenzaldehyde. After the addition was complete, the reaction was continued for 1 hour, and then 27.7 g of p-hydroxybenzaldehyde was added. After the addition was completed, the reaction was incubated at 45°C for 5 hours.

[0039] Add 400 mL of acetonitrile, stir and cool down to 15°C, adjust the pH of the reaction solution to 5-6 with 18% aqueous hydrochloric acid, and a yellow solid precipitates. Filter, wash the filter cake once with 50mL of cold absolute ethanol, once with 50mL of petroleum ether, and dry to obtain 136.85g of a ye...

Embodiment 2

[0040] Example 2: Synthesis of 1-[2-hydroxyl-4-(3-methyl-2-butenyloxy)-phenyl]-3-(4-hydroxyphenyl)-propenone (IV)

[0041]In a 3000mL reaction flask equipped with stirring, condenser, thermometer and dropping funnel, add 200g of 2-hydroxy-4-(3-methyl-2-butenyloxy)acetophenone and 750mL of absolute ethanol, start stirring , Add 1450 mL of 10% aqueous sodium hydroxide solution. After the reaction system was dissolved, slowly add 55g of p-hydroxybenzaldehyde. After the addition was complete, the reaction was continued for 1.5 hours, and then 55g of p-hydroxybenzaldehyde was added. After the addition was completed, the reaction was incubated at 25°C for 10 hours.

[0042] Add 400 mL of acetonitrile, stir and cool down to 15°C, adjust the pH of the reaction solution to 5-6 with 18% aqueous hydrochloric acid, and a yellow solid precipitates. Filter, wash the filter cake once with 50mL of cold absolute ethanol, once with 50mL of petroleum ether, and dry to obtain 234.62g of a yell...

Embodiment 3

[0043] Example 3: Synthesis of 1-[2-hydroxyl-4-(3-methyl-2-butenyloxy)-phenyl]-3-(4-hydroxyphenyl)-propenone (IV)

[0044] In a 3000mL reaction flask equipped with stirring, condenser, thermometer and dropping funnel, add 200g of 2-hydroxy-4-(3-methyl-2-butenyloxy)acetophenone and 750mL of absolute ethanol, start stirring , Add 1650 mL of 10% potassium hydroxide aqueous solution. After the reaction system was dissolved, slowly add 138.6g p-hydroxybenzaldehyde. After the addition was complete, the reaction was continued for 2 hours, and then 138.6 g of p-hydroxybenzaldehyde was added. After the addition was completed, the reaction was incubated at 5°C for 15 hours.

[0045] Add 400 mL of acetonitrile, stir and cool down to 15°C, adjust the pH of the reaction solution to 5-6 with 18% aqueous hydrochloric acid, and a yellow solid precipitates. Filter, wash the filter cake once with 50mL of cold absolute ethanol, once with 50mL of petroleum ether, and dry to obtain 270.0g of a ...

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Abstract

The invention pertains to the technical field of chemical pharmaceutical production and particularly provides a novel preparation method of sofalcone which has a general formula (I) structure and is mainly applied to the treatment of gastric ulcer and chronic gastritis. The preparation method adopts 2-hydroxy-4-(3-methyl-2-butene oxygen) hypnone as a starting material and a target compound sofalcone (I) is finally prepared after reactions with four steps. Compared with synthesis technologies provided by the existing literatures, the method simplifies the processing method of intermediate products, improves the quality and yield of products and reduces costs.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to a novel preparation method of sofalone. Background technique [0002] Sofalcone (Sofalcone) is a kind of medicine for the treatment of gastric ulcer and chronic gastritis researched and developed by Japan Taisho Pharmaceutical Co., Ltd. According to the chemical structure of the anti-ulcer components contained in the traditional Chinese medicine broad bean root, it is a chalcone derivative compound with a strong prenyl skeleton that is screened from a series of derivatives synthesized. [0003] Chemical name: [5-(3-methyl-2-butenyloxy)-2-[3-[4-(3-methyl-2-butenyloxy)phenyl]-1-oxide-2 -propenyl]phenoxy]acetic acid [0004] Molecular formula: C 27 h 30 o 6 [0005] Molecular weight: 450.5 [0006] Chemical structure: [0007] [0008] Sofadone is an effective gastric mucosal protective agent, which can increase gastric blood flow, dilate gastric muc...

Claims

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Application Information

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IPC IPC(8): C07C59/125C07C51/347C07C51/367
Inventor 刘颖刘登科刘默黄汉忠帅军杨妙邹美香吴疆
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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