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Preparation method of dihydrooat alkaloid

A technology of oat alkaloids and dihydrogen, which is applied in the field of preparation of dihydrooat alkaloids, can solve problems such as corrosion and expensive acetoxyphenylpropionate, and achieve the effects of high reaction purity, low reaction temperature, and increased yield

Pending Publication Date: 2022-04-08
重庆美杉蓝科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, a variety of methods for synthesizing hydroxyphenylpropionamide benzoic acid have been reported, wherein the method reported by CN106631865,2017, A has more industrial value, but the raw material acetoxyphenylpropionic acid is more expensive, and the three-step total yield is in About 67.8%, of which thionyl chloride is used, which has a certain corrosion effect on equipment

Method used

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  • Preparation method of dihydrooat alkaloid
  • Preparation method of dihydrooat alkaloid
  • Preparation method of dihydrooat alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Into the reaction flask, put 33.24g (0.2mol) of p-hydroxyphenylpropionic acid, 150mL of dichloromethane and 5.0g (0.02mol) of pyridinium p-toluenesulfonate, and slowly add 15.87g (0.22mol) of p-toluenesulfonate at a controlled temperature of 15-20°C After the addition of vinyl ether / dichloromethane mixed solution, control the temperature at 20-25 ° C for 5 hours, TLC detects that there is no raw material remaining, wash with saturated saline solution, and concentrate the organic phase to no liquid to obtain 3-(4- (1-Ethoxyethoxy)phenyl)propanoic acid 46.08g, yield 96.7%, HPLC 95.3%. 1 HNMR (400MHz, CDCl 3 ):11.93(s,1H),7.15-7.11(m,2H),6.87-6.84(m,2H),5.60-5.65(m,1H),3.86-3.82(m,2H),2.73-2.69(m ,2H),2.51-2.48(m,2H),1.61-1.58(m,3H),1.20-1.17(m,3H).

Embodiment 2

[0039]

[0040] Into the reaction flask, put 33.24g (0.2mol) of p-hydroxyphenylpropionic acid, 150mL of dichloromethane and 5.0g (0.02mol) of pyridinium p-toluenesulfonate, and slowly add 18.95g (0.22mol) of p-toluenesulfonate at a temperature of 15-20°C Vinyl isopropyl ether / dichloromethane mixed solution, after the addition is complete, control the temperature at 20-25 ° C for 5 hours, and TLC detects that there is no raw material remaining, wash with saturated saline solution, and concentrate the organic phase to no liquid to obtain 3-( 4-(1-isopropoxyethoxy)phenyl)propanoic acid 49.0g, yield 97.1%, HPLC 94.8%.

Embodiment 3

[0042]

[0043] Into the reaction bottle, put 33.24g (0.2mol) of p-hydroxyphenylpropionic acid, 150mL of dichloromethane and 5.0g (0.02mol) of pyridinium p-toluenesulfonate, and slowly add 18.95g (0.22mol) ) Vinyl n-propyl ether / dichloromethane mixed solution, after the addition, control the temperature at 20-25°C for 5 hours of reaction, TLC detects that there is no raw material remaining, washing with saturated saline solution, and concentrating the organic phase to no liquid to obtain 3- (4-(1-n-propoxyethoxy)phenyl)propanoic acid 48.5g, yield 96.1%, HPLC 95.8%.

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Abstract

The invention discloses a preparation method of dihydrooat alkaloid, and belongs to the technical field of organic synthesis. Hydroxyl is protected by p-hydroxyphenylpropionic acid and vinyl alkyl ether under the action of a catalyst, then the p-hydroxyphenylpropionic acid and anthranilate are condensed under the action of the catalyst to generate acid amine, and then the dihydrooat alkaloid is obtained through inorganic alkali / acid deprotection or acid deprotection. The method is completed in three steps, the product is easy to separate, the total yield of the three steps is up to 80-85%, the reaction is coherent, the used reagent is friendly to equipment, and the product purity can reach 99.8%.

Description

technical field [0001] The invention relates to a preparation method of dihydrooat alkaloid, which belongs to the technical field of organic synthesis. Background technique [0002] Avenous alkaloids are divided into A~G types; hydroxyphenylpropanamide benzoic acid, dihydroavenous alkaloid D, CAS697235-49-7, English name: 2-[3-(4-hydroxyphenyl)propanoyl amino]benzoic Acid, whose structure is similar to that of oat alkaloids, has the properties of antihistamine activity, inhibition and inflammation of oat alkaloids, and can greatly reduce the itching frequency of contact dermatitis and neurodermatitis. It is currently used for anti-irritation and antipruritic No side effects were found in the product. [0003] [0004] [0005] Due to the low content of oat alkaloids in oats and other crops, relying solely on natural product sources cannot meet the growing needs of industrial production. Hydroxyphenylpropionamide benzoic acid is similar to natural oat alkaloids, and ca...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C235/38C07C231/02
Inventor 童华陈天豪邓恩元周芝凤张培
Owner 重庆美杉蓝科技发展有限公司
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