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A kind of method for preparing vilanterol

A tetrahydrofuran, molar ratio technology, applied in the preparation of carboxylate, carboxylic acid amide, organic chemical methods, etc., can solve the problems of the difficulty of chiral purity to meet the quality requirements, the difficulty of chiral center construction, and the limitation of industrial applications. Achieve the effects of avoiding the use of protective groups, increasing atom utilization, and low production costs

Active Publication Date: 2021-07-27
ANHUI DEXINJIA BIOPHARM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this route synthesis step is longer, wherein needs to use a plurality of protecting groups, functional group protection and deprotection have increased reaction steps, and wherein also use bis (tert-butoxycarbonyl) amine to remove a tert-butoxycarbonyl again, The low utilization rate of atoms leads to low synthesis yield, which limits its industrial application, and the construction of chiral centers is difficult, and the chiral purity meets the quality requirements.

Method used

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  • A kind of method for preparing vilanterol
  • A kind of method for preparing vilanterol
  • A kind of method for preparing vilanterol

Examples

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Embodiment 1

[0023] Preparation of Intermediate 1:

[0024] Add 200mL water to a 500mL three-necked flask, add 13.2g (1.1eq) sodium hydroxide in batches, cool to 0-5°C, add 37.2g (1eq) salicyl alcohol while stirring, and then add 0.68g (1%) Benzyltriethylammonium chloride, fully stirred for 1 hour, under the condition of 0-5 ℃, slowly added 44.4g of 50% glyoxylic acid aqueous solution into the reaction system dropwise within 1 hour, and the temperature of the reaction system rose to 25 ℃, continue to react for 6 hours, and the remaining raw materials in the liquid phase are less than 1%, and the reaction is completed. Cool the system to 0-5°C, adjust the pH to 2-3 with concentrated hydrochloric acid, extract with 100×2 mL of tert-butyl acetate, combine the organic phases, wash with 100 mL of saturated saline, 100 mL of water, dry over anhydrous magnesium sulfate, and filter. Concentration gave a white solid, and the crude product was recrystallized from toluene to obtain 50 g, with a yiel...

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Abstract

The invention discloses a method for preparing vilanterol, which belongs to the field of drug synthesis. The method comprises the following steps: (1) addition reaction of salicyl alcohol and glyoxylic acid to generate intermediate 1; (2) intermediate 1 undergoes chiral resolution to obtain chiral intermediate 2; (3) intermediate 2 and intermediate Intermediate 3 undergoes acylation reaction to generate intermediate 4, wherein intermediate 3 is obtained by Delbin reaction of intermediate 5; (4) intermediate 4 is reduced to obtain vilanterol. The invention has easy-to-obtain raw materials, short synthesis route, reduced production cost, mild reaction conditions, simple operation and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of drug synthesis and relates to a method for preparing vilanterol. Background technique [0002] Vilanterol trifenatate (Vilanterol trifenatate) is a long-acting beta 2 receptor agonists. 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. The molecular weight of vilanterol is 486.4, the molecular formula is C24H33Cl2NO5, CAS: 503068-34-6, the Chinese name is: chemical name: (R)-4-[2-[[6-[(2,6-dichlorobenzyl ) Oxygen]-Ethoxy]Ethyl]Amino]-1-Hydroxyethyl]-2-Hydroxyethyl]-2-Hydroxymethylphenol, the chemical structure is as follows: [0003] [0004] The world patent WO2003024439 relates to a method for synthesizing vilanterol, the specific synthetic route is as follows: [0005] [0006] This synthetic route is the original research rou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/02C07C217/08C07C231/02C07C235/34C07C51/367C07C51/487C07C59/52C07B57/00
CPCC07B57/00C07B2200/07C07C51/367C07C51/487C07C213/02C07C231/02C07C217/08C07C235/34C07C59/52
Inventor 张启龙许坤郑庚修高令峰诸葛文云
Owner ANHUI DEXINJIA BIOPHARM
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