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A kind of preparation method and its intermediate of 2-methyl-2'-phenylpropionic acid derivative

A technology of phenylpropionic acid and its derivatives, which is applied in the medical field, can solve problems such as increased raw material costs, purification, and cumbersome process, and achieves the effects of simple and efficient preparation methods, easy industrial production, and low cost

Active Publication Date: 2020-07-03
LUOXIN PHARM SHANGHAI CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 2-Methyl-2'phenylpropionic acid derivatives uniquely have H 1 Antihistamine activity, thus, does not require interaction with other drug receptors, shows high selectivity even at high doses, has antihistamine properties but no sedative or cardiovascular effects
However, in the preparation process of this method, the elimination reaction of key intermediates inevitably occurs, which makes the whole process quite cumbersome, the requirements of reaction conditions are strict and difficult to control, and a large number of side reactions not only increase the cost of raw materials, but also a large number of The by-product also brings purification problem, therefore, this method is used for the productive rate of the 2-methyl-2'-phenylpropionic acid derivative of industrial scale preparation formula 1 is very low

Method used

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  • A kind of preparation method and its intermediate of 2-methyl-2'-phenylpropionic acid derivative
  • A kind of preparation method and its intermediate of 2-methyl-2'-phenylpropionic acid derivative
  • A kind of preparation method and its intermediate of 2-methyl-2'-phenylpropionic acid derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: Preparation of 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid methyl ester

[0068] In a reaction vessel, add 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid (5.0 g), methanol (50 mL) and concentrated sulfuric acid (0.5 mL) and heat to 80°C, stirred and reacted for 20 hours, cooled to room temperature, added dropwise saturated sodium carbonate aqueous solution, adjusted the pH to neutral, concentrated until no more liquid dripped, added 30mL water and stirred for 1 hour, added 10mL ethyl acetate for extraction three times, and combined the organic phases , washed with 10 mL of saturated brine, the organic phase was separated, dried with 2 g of anhydrous sodium sulfate for 2 hours, filtered, and the filtrate was concentrated under reduced pressure to obtain 2-methyl-2-(4-(2-hydroxyethyl)-phenyl) - Methyl propionate (5.3 g, 100% yield).

[0069] 1 HNMR, 500MHZ, CDCl 3 , ppm: 1.56(s, 6H), 2.03(t, 1H), 2.82(t, 2H), 3.64(s, 3H), 3.82(t, 2H), 7.1...

Embodiment 2

[0070] Embodiment 2: Preparation of 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid methyl ester

[0071] In a reaction vessel, 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid (2.5 g), dimethylformamide (12.5 mL) and potassium carbonate (5 g ), stirred at room temperature, added dropwise methyl iodide (2.0g), stirred at room temperature for 4 hours, added 30mL of water, stirred for 30 minutes, added 5mL of ethyl acetate for extraction three times, combined the organic phases, washed three times with 10mL of saturated brine, separated organic phase, dried with 1g of anhydrous sodium sulfate for 4 hours, filtered, and the filtrate was concentrated under reduced pressure to obtain 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid methyl ester (2.7g, yield rate 100%).

[0072] 1 HNMR, 500MHZ, CDCl 3 , ppm: 1.56(s, 6H), 2.03(t, 1H), 2.82(t, 2H), 3.64(s, 3H), 3.82(t, 2H), 7.17(d, 2H), 7.27(d, 2H ). MS(ESI):[M+H] + =222.98

Embodiment 3

[0073] Embodiment 3: Preparation of 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid ethyl ester

[0074] In a reaction vessel, add 2-methyl-2-(4-(2-hydroxyethyl)-phenyl)-propionic acid (2.5 g), ethanol (25 mL) and concentrated sulfuric acid (0.3 mL) and heat to 80°C, stirred and reacted for 22 hours, cooled to room temperature, added dropwise saturated sodium carbonate aqueous solution, adjusted the pH to neutral, concentrated until no more dripping, added 10mL water and stirred for 1 hour, added 5mL ethyl acetate for extraction three times, combined the organic phases , washed with 5 mL of saturated brine, separated the organic phase, dried with 1 g of anhydrous sodium sulfate for 3 hours, filtered, and the filtrate was concentrated under reduced pressure to obtain 2-methyl-2-(4-(2-hydroxyethyl)-phenyl) - Ethyl propionate (2.8 g, 100% yield).

[0075] MS(ESI):[M+H] + =237.03

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Abstract

The invention relates to a preparation method and intermediate of a 2-methyl-2'-phenylpropionic acid derivative. The method is simple, efficient, little in side reaction, high in yield, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to the medical field, in particular to a preparation method of a 2-methyl-2'-phenylpropionic acid derivative and a new intermediate compound thereof. Background technique [0002] The 2-methyl-2'-phenylpropionic acid derivatives of the following formula 1 are widely used in the pharmaceutical field. [0003] [Formula 1] [0004] [0005] Among them, R 2 Hydrogen or -CH 2 CH 2 OR 3 ; 3 C for branched or straight chain 1 -C 10 alkyl. [0006] 2-Methyl-2'phenylpropionic acid derivatives uniquely have H 1 Antihistamine activity, thus, does not require interaction with other drug receptors, shows high selectivity even at high doses, has antihistamine properties but no sedative or cardiovascular effects. Therefore, 2-methyl-2'-phenylpropionic acid derivatives can be used in patients with allergic diseases, especially those taking other drugs at the same time, such as those with cardiovascular diseases. [0007] CN 10195227...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07C59/74C07C69/73
CPCC07C59/74C07C69/738C07D401/04
Inventor 杨文谦唐伟詹祖金杨旭王铁林
Owner LUOXIN PHARM SHANGHAI CO LTD
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