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Synthesis method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl] methyl benzoate

A technology of methyl benzoate and hydroxypropyl, applied in the field of compound synthesis, can solve the problems of undisclosed chiral purity of intermediates, and the yield needs to be improved, and achieves reduction of synthesis cost, high recovery rate, and solution of metal residual risks. Effect

Pending Publication Date: 2020-08-25
ENANTIOTECH CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method needs to be carried out under relatively high pressure conditions, which inevitably poses challenges for scale-up production, and the yield needs to be improved
At the same time, as a drug, montelukast sodium is closely related to its chiral purity and drug efficacy, and this method does not specifically disclose the chiral purity of its prepared intermediates, which needs further study

Method used

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  • Synthesis method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl] methyl benzoate
  • Synthesis method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl] methyl benzoate
  • Synthesis method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl] methyl benzoate

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preparation example Construction

[0062] The present invention also provides a synthetic method of montelukast sodium, the steps comprising: adopting the synthetic method as described above to synthesize (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxy Propyl]methylbenzoate.

[0063] Montelukast sodium is an oral leukotriene receptor antagonist, which can specifically inhibit the cysteinyl leukotriene (CysLT1) receptor in the airway, thereby improving airway inflammation and effectively controlling asthma symptoms. Montelukast sodium is a non-hormonal anti-inflammatory drug, suitable for the prevention and long-term treatment of asthma and the treatment of allergic rhinitis in adults and children over 1 year old. Synthesizing the important intermediate of montelukast sodium through the above method can effectively improve the chiral purity of the final product montelukast sodium, which is undoubtedly of great significance for the improvement of its drug efficacy and the reduction of side effects. At the same time, th...

Embodiment 1

[0068] This embodiment is a synthetic method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl]methyl benzoate, the steps are as follows:

[0069] (1) In the 5L autoclave, feed argon to replace the air to form an argon atmosphere, add 100g raw material methyl-2-[3-(3-bromophenyl)-3 from the feed port of the autoclave -Oxopropyl] methyl benzoate, then add 1L of toluene to fully dissolve the raw material, continue to pass in argon gas for bubbling degassing, continue bubbling for 1h, and degassing is completed.

[0070] (2) Under argon atmosphere, add 0.05g catalyst (wherein, the degree of polymerization of PEG n=160) from the feed port of the autoclave, and finally add 10g potassium ethylate, after the feed is completed, quickly close the feed port.

[0071] (3) Replace the argon in the autoclave with hydrogen, then slowly feed hydrogen until the pressure in the autoclave is 3 atm, close the inflation valve; stir and react rapidly at a temperature of 30°C. During the reaction...

Embodiment 2

[0075] This embodiment is a synthetic method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl]methyl benzoate, the steps are as follows:

[0076] (1) In the 5L autoclave, feed argon to replace the air to form an argon atmosphere, add 100g raw material methyl-2-[3-(3-bromophenyl)-3 from the feed port of the autoclave -Oxopropyl] methyl benzoate, then add 1L of toluene to fully dissolve the raw material, continue to pass in argon gas for bubbling degassing, continue bubbling for 1h, and degassing is completed.

[0077] (2) Under an argon atmosphere, add 0.05 g of catalyst (wherein, the degree of polymerization of PEG n=150) from the feed port of the autoclave, and finally add 10 g of potassium ethylate, and close the feed port quickly after the feed is completed.

[0078](3) Replace the argon in the autoclave with hydrogen, then slowly feed hydrogen until the pressure in the autoclave is 3 atm, close the inflation valve; stir and react rapidly at a temperature of 30°C. During...

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Abstract

The invention relates to a preparation method of (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl] methyl benzoate. The preparation method comprises the following step: carrying out asymmetric hydrogenation reaction on methyl-2-[3-(3-bromophenyl)-3-oxopropyl] methyl benzoate under the catalysis of a catalyst; and the catalyst has structural characteristics as shown in the following formula (I). The(S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl] methyl benzoate product prepared by the preparation method is higher in chiral purity and long in service life, the reaction can be carried out underthe condition of lower pressure, large-scale production and application are facilitated, the adopted catalyst can be recycled, heavy metal pollution is avoided, and the cost is reduced.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a method for synthesizing methyl (S)-methyl-2-[3-(3-bromophenyl)-3-hydroxypropyl]benzoate. Background technique [0002] The common name is montelukast sodium, which is an oral leukotriene receptor antagonist, which can specifically inhibit the cysteinyl leukotriene (CysLT1) receptor in the airway, so as to improve airway inflammation and effectively control Asthma symptoms. Montelukast sodium is a non-hormonal anti-inflammatory drug, suitable for the prevention and long-term treatment of asthma and the treatment of allergic rhinitis in adults and children over 1 year old. According to the recommendation of the 2008 edition of my country's "Guidelines for the Prevention and Treatment of Bronchial Asthma", leukotriene modulators are the only long-term control drugs that can be used alone in addition to inhaled hormones. Therefore, the synthesis of montelukast sodium...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/78C07D215/18
CPCC07C67/31C07D215/18C07B2200/07Y02P20/584
Inventor 毛波徐亮蒙发明文浩力赖显春卢锦宏
Owner ENANTIOTECH CORP
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