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A simple and efficient method for synthesizing 4-arylbutyric acid derivatives

A technology for aryl butyric acid and derivatives, which is applied in the field of simple and efficient synthesis of 4-aryl butyric acid derivatives, can solve the problems of too many additives, lengthy synthesis steps, harsh reaction conditions, etc., and solve the cumbersome steps of the synthesis process , high product yield and mild reaction conditions

Active Publication Date: 2021-11-23
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported catalytic synthesis systems have many shortcomings, such as: narrow substrate range, harsh reaction conditions, excessive amount of additives, lengthy synthesis steps, relatively low yield, etc.

Method used

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  • A simple and efficient method for synthesizing 4-arylbutyric acid derivatives
  • A simple and efficient method for synthesizing 4-arylbutyric acid derivatives
  • A simple and efficient method for synthesizing 4-arylbutyric acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Under air conditions, 0.2mmol N-(8-aminoquinoline) but-3-enamide, 0.4mmol phenyltrimethoxysilane, 0.02mmol palladium acetate, 0.4mmol copper fluoride, 2.0mmol acetic acid And 2.0mL tetrahydrofuran is added into the reaction vessel and mixed and stirred evenly; the reaction vessel is a pressure-resistant sealed tube containing a magnetic stirrer;

[0029] (2) After sealing the reaction vessel, put it into an oil bath at 100° C. to vigorously stir for 24 hours, TLC (developing agent is V 石油醚 :V 乙酸乙酯 =9:1) The detection substrate disappears and the reaction ends. The reaction solution was poured into saturated brine (15mL), extracted with dichloromethane (3×10mL), the combined organic phases were dried over anhydrous sodium sulfate, suction filtered, vacuum distillation, etc., and subjected to silica gel column chromatography (eluent for V 石油醚 :V 乙酸乙酯 =9:1) to obtain a colorless solid, the target product was 1 H NMR, 13 C NMR test proved that it was 4-arylbutanoi...

Embodiment 2

[0031] (1) Under air conditions, 0.2mmol N-(8-aminoquinoline) but-3-enamide, 0.4mmol 4-methylphenyltrimethoxysilane, 0.02mmol palladium acetate, 0.4mmol copper fluoride , 2.0mmol acetic acid and 2.0mL tetrahydrofuran were added to the reaction vessel and mixed and stirred evenly; the reaction vessel was a pressure-resistant sealed tube containing a magnetic stirrer;

[0032] (2) After sealing the reaction vessel, put it into an oil bath at 100° C. to vigorously stir for 24 hours, TLC (developing agent is V 石油醚 :V 乙酸乙酯 =9:1) The detection substrate disappears and the reaction ends. The reaction solution was poured into saturated brine (15mL), extracted with dichloromethane (3×10mL), the combined organic phases were dried over anhydrous sodium sulfate, suction filtered, vacuum distillation, etc., and subjected to silica gel column chromatography (eluent for V 石油醚 :V 乙酸乙酯 =9:1) to obtain a colorless solid, the target compound was 1 H NMR, 13 C NMR test proved that it was 4-...

Embodiment 3

[0034] (1) Under air conditions, 0.2mmol N-(8-aminoquinoline) but-3-enamide, 0.4mmol 4-fluorophenyltrimethoxysilane, 0.02mmol palladium acetate, 0.4mmol copper fluoride, Add 2.0mmol acetic acid and 2.0mL tetrahydrofuran into the reaction vessel and mix well; the reaction vessel is a pressure-resistant sealed tube containing a magnetic stirrer;

[0035] (2) After sealing the reaction vessel, put it into an oil bath at 100° C. to vigorously stir for 24 hours, TLC (developing agent is V 石油醚 :V 乙酸乙酯 =9:1) The detection substrate disappears and the reaction ends. The reaction solution was poured into saturated brine (15mL), extracted with dichloromethane (3×10mL), the combined organic phases were dried over anhydrous sodium sulfate, suction filtered, vacuum distillation, etc., and subjected to silica gel column chromatography (eluent for V 石油醚 :V 乙酸乙酯 =9:1) to obtain a colorless solid, after 1 H NMR, 13 C NMR test proved that it was 4-arylbutanoic acid derivative 3c, and the ...

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Abstract

The invention discloses a simple and efficient method for synthesizing 4-arylbutyric acid derivatives. Removable 8-aminoquinoline is used as a guiding group to control the regioselectivity of the reaction, and non-activated 3-butenamide is used. As a reaction raw material, it reacts with cheap, readily available, stable and efficient aryltrimethoxysilane to prepare and synthesize a series of functionalized 4-arylbutyric acid derivatives concisely and efficiently. The method has the advantages of simple operation, simple and easy-to-obtain reaction raw materials, easy separation and purification of products, high product yield and good reaction zone selectivity. The invention can provide related products for treating urea cycle disorder, novel anti-type II diabetes drugs, angiotensin-converting enzyme inhibitors and the like, and has good market potential and application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a simple and efficient method for synthesizing 4-aryl butyric acid derivatives. Background technique [0002] Carboxylic acids and their derivatives are widely found in molecules such as medicines, pesticides, and natural products. Many carboxylic acids and their derivatives themselves are small organic drug molecules with specific physiological activities, and are used to treat leukemia, hypertension, ovarian cancer, common diseases such as diabetes. 4-Arylbutyric acid and its derivatives are one of the important categories, such as sodium phenylbutyrate (Buphenyl) is an important prodrug, which is used to treat urea cycle disorders, which can effectively reduce blood ammonia and blood glutamine Acid content; Chlorambucil is used to treat Hodgkin's disease, multiple non-Hodgkin's lymphomas, chronic lymphocytic leukemia, Waldenstrom's macroglobulinemia, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40
CPCC07D215/40
Inventor 卢明祝罗海青胡正松邵长栋阚玉和
Owner HUAIYIN TEACHERS COLLEGE
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