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Method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester

A technology of methyl biphenyl and methyl carboxylate, which is applied in the preparation of carboxylate, carboxylate/lactone, and oxygenated compounds, etc., can solve the problem of reducing product yield, multi-solid waste residue, environmental pollution, etc. problem, to achieve the effect of improving yield, low cost and reducing pollution

Inactive Publication Date: 2019-10-25
河南华商药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] After this route is synthesized to the final product 4'-methylbiphenyl-2-carboxylate methyl ester, a lot of solid waste residues will be produced, which not only reduces the product yield, but also causes certain pollution to the environment

Method used

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  • Method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester
  • Method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester
  • Method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 4'-methylbiphenyl-2-methyl carboxylate waste residue (main content: 49%) 20.2g, sodium hydroxide 12.3g, drinking water 58.7g in the 250ml four-necked flask, heat up to 80 DEG C and hydrolyze for 10 hours, HPLC detects 0.28% of 4'-methylbiphenyl-2-methyl carboxylate remaining; cool down to below 30°C, add 41.4g of dichloromethane, stir for 30min, let stand for 30min, separate the lower solvent layer, add the upper aqueous layer To 40.9 g of dichloromethane, 38.6 g of 31% hydrochloric acid was added dropwise with stirring to adjust the pH to 1. Continue to stir for 30 minutes, let stand for 30 minutes, separate the lower dichloromethane layer (the content of 4'-methylbiphenyl-2-carboxylic acid detected by HPLC is 98.2%) and evaporate to dryness, then add methanol 10.5g, continue to evaporate to dryness; evaporate to dryness Finally, add methanol 31.2g, sulfuric acid 9.8g, reflux and stir for 5 hours, the content of 4′-methylbiphenyl-2-carboxylate methyl ester detected...

Embodiment 2

[0023] Add 4'-methylbiphenyl-2-methyl carboxylate waste residue (main content: 73%) 20.3g, sodium hydroxide 12.0g, drinking water 58.1g in the 250ml four-necked flask, heat up to 80 DEG C and hydrolyze for 10 hours, HPLC detects 0.31% of 4'-methylbiphenyl-2-methyl carboxylate remaining; cool down to below 30°C, add 40.5g of dichloromethane, stir for 30min, let stand for 30min, separate the lower solvent layer, add the upper aqueous layer To 41.0 g of dichloromethane, 39.2 g of 31% hydrochloric acid was added dropwise with stirring to adjust the pH to 1. Continue to stir for 30 minutes, let stand for 30 minutes, separate the lower dichloromethane layer (the content of 4'-methylbiphenyl-2-carboxylic acid detected by HPLC is 98.8%) and evaporate to dryness, then add 11.0 g of methanol, and continue to evaporate to dryness; Finally, add methanol 30.7g, sulfuric acid 10.0g, reflux and stir for 5 hours, the content of 4'-methylbiphenyl-2-carboxylate methyl ester detected by HPLC is ...

Embodiment 3

[0025] Add 4'-methylbiphenyl-2-methyl carboxylate waste residue (main content: 49%) 20.0g, sodium hydroxide 16.6g, drinking water 61.3g in the 250ml four-necked flask, heat up to 80 DEG C and hydrolyze for 15 hours, 0.09% of 4′-methylbiphenyl-2-carboxylate methyl ester was detected by HPLC; the temperature was lowered to below 30°C, 40.7g of dichloromethane was added, stirred for 30min, left standing for 30min, the lower solvent layer was separated, and the upper aqueous layer was added To 42.2 g of dichloromethane, 35.0 g of 31% hydrochloric acid was added dropwise with stirring to adjust the pH to 1. Continue to stir for 30 minutes, let stand for 30 minutes, separate the lower dichloromethane layer (the content of 4'-methylbiphenyl-2-carboxylic acid detected by HPLC is 98.9%) and evaporate to dryness, then add methanol 11.5g, continue to evaporate to dryness; evaporate to dryness Finally, add methanol 30.0g, sulfuric acid 10.1g, reflux and stir for 6 hours, the content of 4′...

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Abstract

The invention relates to a method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester, and belongs tothe technical field of pharmaceutical synthesis. According to the method, the waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester are taken as starting materials, after alkali hydrolysis, acidolysis and then layering are carried out after solvent extraction, after the solvent extraction, layering and re-esterification processes are carried out to synthesize the high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester. By using the method, the waste residues are recycled, the reuse of the waste residues is realized, the overall yield of the reaction is improved, and the pollution is reduced; and the method is low in cost, easy in operation and easy to realize industrial production.

Description

technical field [0001] The invention relates to a method for preparing high-purity methyl 4'-methylbiphenyl-2-carboxylate using 4'-methylbiphenyl-2-carboxylate waste residue, which belongs to the technical field of pharmaceutical synthesis. Background technique [0002] Telmisartan is a drug for the treatment of mild to moderate hypertension. A number of clinical trials have proved that Telmisartan has a good effect on the treatment of patients with high-risk cardiovascular diseases. It has a similar effect to ramipril, which is currently regarded as the gold standard. role, thus promoting its rapid rise in the market. And as synthetic telmisartan key intermediate brominated biphenyl compound, used brominated biphenyl carboxylate tert-butyl ester (1) as intermediate material in EP0502314, used methyl brominated biphenyl carboxylate in the patent CN1344712 (2), and bromosartan biphenyl (3) is used as a key intermediate in the CN1412183 patent, and methyl bromobiphenylcarboxy...

Claims

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Application Information

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IPC IPC(8): C07C67/60C07C67/08C07C69/76C07C51/09C07C27/02C07C63/331
CPCC07C51/09C07C67/08C07C67/60C07C69/76C07C63/331
Inventor 夏冬邢学达侯一凡夏玉良
Owner 河南华商药业有限公司
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