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Method for synthesizing 2-methacrylate derivatives by use of ester compounds

The technology of a compound and a palladium compound is applied in the field of synthesis of pharmaceutical intermediates, and can solve the problems of difficulty in purchasing raw material tin compounds, large pollution, etc., and achieve the effects of being beneficial to large-scale production, reducing energy consumption, and easily obtaining raw materials

Inactive Publication Date: 2014-11-19
CHONGQING HUAPONT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] This method has many steps (two-step reaction), and the raw material tin compound is difficult to purchase, and the pollution is relatively large

Method used

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  • Method for synthesizing 2-methacrylate derivatives by use of ester compounds
  • Method for synthesizing 2-methacrylate derivatives by use of ester compounds
  • Method for synthesizing 2-methacrylate derivatives by use of ester compounds

Examples

Experimental program
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Effect test

Embodiment 12-4

[0055] The synthesis of embodiment 12-[4-[2-(ethoxy) ethyl] phenyl]-2-methoxybenzyl propionate

[0056] Add the toluene solution containing 14.14g lithium bistrimethylsilylamide to the reaction flask, then add 70.37g p-methoxybenzyl isobutyrate (formula III, R2 is p-methoxybenzyl), after stirring for 10 minutes, Add 10.4g4-[2-(ethoxy)ethyl]chlorobenzene (formula II, R1 is ethyl, X is chlorine) and 4.5mg dibromobis(tri-tert-butylphosphine)palladium(I), in After reacting for 40 minutes at 20-30 degrees, the raw material 4-[2-(ethoxy)ethyl]chlorobenzene was detected by HPLC method and disappeared. After the reaction is complete, add 1mol / L hydrochloric acid to the reaction solution to precipitate a solid, filter and retain the filtrate, separate the organic layer from the filtrate, and concentrate to obtain 2-[4-[2-(ethoxy)ethyl]phenyl] - 15.85 g of p-methoxybenzyl 2-methylpropionate, the molar yield is 91.2%.

Embodiment 22-4

[0057] The synthesis of embodiment 22-[4-[2-(cyclohexyloxy) ethyl] phenyl]-2-methyl propionate

[0058] Add 3.88g of tetrahydrofuran solution containing lithium diisopropylamide to the reaction flask, then add 3.70g of methyl isobutyrate (formula III, R2 is methyl), stir for 12 minutes, then add 20.5g of 4-[2 -(cyclohexyloxy) ethyl] bromobenzene (formula II, R1 is cyclohexyl, X is bromine) and 0.8365g tetrakis (triphenylphosphine) palladium (0), reacted for 60 minutes at 15-25 degrees, The HPLC method detected that the raw material 4-[2-(cyclohexyloxy)ethyl]bromobenzene had disappeared. After the reaction is complete, add 1mol / L hydrochloric acid to the reaction solution to precipitate a solid, filter and retain the filtrate, separate the organic layer from the filtrate, and concentrate to obtain 2-[4-[2-(cyclohexyloxy)ethyl]phenyl ]-21.51g of methyl propionate, molar yield 97.6%.

Embodiment 32-4

[0059] Synthesis of Example 32-[4-[2-(benzyloxy)ethyl]phenyl]-2-methylpropionic acid isopropyl ester

[0060]Add the ethylene glycol dimethyl ether solution containing 55.30g of lithium dicyclohexylamide to the reaction flask, then add 7.69g of isopropyl isobutyrate (formula III, R2 is isopropyl), and stir for 8 minutes. Add 8.6g 4-[2-(benzyloxy)ethyl]bromobenzene (formula II, R1 is benzyl, X is bromine) and 34.1mg tetrakis(triphenylphosphine) palladium (0), at 0-10 degrees The reaction was carried out for 110 minutes, and the raw material 4-[2-(benzyloxy)ethyl]bromobenzene had disappeared as detected by HPLC. After the reaction is complete, add 1mol / L hydrochloric acid to the reaction solution to precipitate a solid, filter and retain the filtrate, separate the organic layer from the filtrate, and concentrate to obtain 2-[4-[2-(benzyloxy)ethyl]phenyl] -9.70 g of isopropyl 2-methylpropionate, the molar yield is 96.5%.

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Abstract

The invention provides a method for synthesizing 2-methacrylate derivatives by use of ester compounds as one of raw materials. The method is characterized in that isobutyrates are creatively selected as one of reaction raw materials instead of alkene compounds in the prior art. The method is capable of obtaining the desired products through only one step of reaction, and is short in reaction time, and low in energy consumption and cost, the reaction can be carried out at a room temperature, and the raw material isobutyrates are easy to get; as a result, the method is greatly convenient for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing 2-methyl propionate derivatives by using an ester compound as one of the raw materials. Background technique [0002] The compound of formula I (2-methyl propionate derivative) is an important intermediate for the preparation of a kind of antihistamine: [0003] [0004] Formula I [0005] The methods for synthesizing Formula I in the prior art are not suitable for industrial production. For example, there are problems such as long routes, high energy consumption, long time-consuming, and non-environmental protection. Such as [0006] Prior art one: CN200980105040, its raw material 2 is 1-methoxy-1-(trimethylsilyloxy)-2-methyl-1-propene, which is not easy to buy, and the reaction temperature is higher ( 80 degrees or more), the reaction time is longer (more than 18 hours). [0007] [0008] Prior art two: Synthetic Com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C69/734C07C69/73C07F7/18
CPCY02P20/55C07C67/343C07F7/1892C07C69/734C07C69/73
Inventor 罗炼占肖沈红梅
Owner CHONGQING HUAPONT PHARMA
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