A kind of synthetic method of vilanterol intermediate

A synthesis method and a technology for intermediates, which are applied in the field of pharmaceutical synthesis, can solve problems such as lowering production costs and reducing vilanterol synthesis steps, and achieve the effects of lowering production costs, shortening synthesis routes, and easily obtaining raw materials

Active Publication Date: 2021-08-20
安徽德信佳济大新药技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] According to domestic and foreign literature reports, there is no synthetic route about 3-hydroxymethyl-4-hydroxymandelic acid at present, therefore, the synthesis of 3-hydroxymethyl-4-hydroxymandelic acid is very important, not only can reduce the Luo synthesis steps, but also greatly reduce production costs

Method used

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  • A kind of synthetic method of vilanterol intermediate
  • A kind of synthetic method of vilanterol intermediate
  • A kind of synthetic method of vilanterol intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 4-hydroxymandelic acid (16.8g), paraformaldehyde (9g) into the there-necked flask, add glacial acetic acid (85mL), FeCl 3 (0.8g), reacted at 80°C for 4h, the reaction in TLC was completed, cooled to room temperature, concentrated the solvent in vacuo, added water (100mL) to the residue, stirred for half an hour, filtered to obtain a solid, and the crude product was recrystallized from ethanol to obtain 13.5 g of 3-hydroxymethyl-4-hydroxymandelic acid, yield 68%, purity 98%.

[0019] Note: 4-Hydroxymandelic acid was purchased from Jiangxi Keyuan Biopharmaceutical Co., Ltd., and the purity of the raw material was 98%.

Embodiment 2

[0021] Add 4-hydroxymandelic acid (50.4g), paraformaldehyde (27g) in the there-necked flask, add trifluoroacetic acid (250mL), ZnCl 2 (2g), reacted at 70°C for 4h, the reaction in TLC was completed, cooled to room temperature, concentrated the solvent in vacuo, added water (200mL) to the residue, stirred for half an hour, filtered to obtain a solid, and the crude product was recrystallized from ethanol to obtain 3 -Hydroxymethyl-4-hydroxymandelic acid 41g, yield 70%, purity 98%.

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Abstract

The invention discloses a method for synthesizing an intermediate of vilanterol, which belongs to the field of drug synthesis. The method uses 4-hydroxymandelic acid as a raw material to obtain 3-hydroxymethyl-4-hydroxymandelic acid through electrophilic substitution reaction. The invention provides a new intermediate of vilanterol, the intermediate raw material is easy to obtain, the operation is simple, and the synthesis of vilanterol by the intermediate greatly shortens the synthetic route, reduces the production cost, and is suitable for industrial production .

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a method for synthesizing the intermediate 3-hydroxymethyl-4-hydroxymandelic acid of the anti-asthma drug vilanterol. Background technique [0002] Vilanterol is a long-acting beta drug developed by GlaxoSmithKline (GSK) 2 receptor agonist. Its compound preparation with fluticasone furoate and its compound preparation with umeclidinium bromide were approved by FDA in May and December 2013, respectively, for the treatment of obstructive pulmonary disease and asthma. Vilanterol has a molecular weight of 486.4 and a molecular formula of C 24 h 33 Cl 2 NO 5 , CAS: 503068-34-6, Chinese name: Chemical name: (R)-4-[2-[[6-[(2,6-dichlorobenzyl)oxy]-ethoxy]ethyl ]amino]-1-hydroxyethyl]-2-hydroxyethyl]-2-hydroxymethylphenol, the chemical structural formula is shown in the figure: [0003] [0004] The world patent WO2003024439 relates to a method for synthesizing vilanterol, the specif...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/52C07C51/367
CPCC07C51/367C07C59/52
Inventor 张启龙郑庚修汪崇文许坤李学坤
Owner 安徽德信佳济大新药技术有限公司
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