Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Empagliflozin intermediate preparation method

A technology for intermediates and compounds, which is applied in the field of preparation of an intermediate of empagliflozin--3-phenoxy)tetrahydrofuran, can solve the problem of high raw material cost, and achieves reduced raw material cost, simple post-processing and little environmental pollution Effect

Pending Publication Date: 2020-01-14
ZHEJIANG HUAYI PHARMA CO LTD OF HANGZHOU HUADONG PHARMA GRP +1
View PDF9 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In the above synthetic route, the raw material (S)-3-hydroxytetrahydrofuran was used earlier, resulting in high raw material cost

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Empagliflozin intermediate preparation method
  • Empagliflozin intermediate preparation method
  • Empagliflozin intermediate preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The invention provides a preparation method of an empagliflozin intermediate. The preparation method uses p-methoxybenzyl chloride and p-iodoaniline as starting materials, and obtains compound IV through substitution, and then undergoes diazotization and Sander Mayer reaction to obtain compound III, further demethylation under the action of boron tribromide to obtain compound II, and finally condensation with (S)-3-p-toluenesulfonyloxytetrahydrofuran to obtain empagliflozin intermediate compound I, specifically including Follow the steps below:

[0050] 1) With p-methoxybenzyl chloride and p-iodoaniline as raw materials, through substitution reaction, the compound 4-iodo-2-(4-methoxybenzyl)aniline shown in formula IV is obtained:

[0051]

[0052] 2) The compound shown in IV is subjected to diazotization and Sandmeyer reaction to obtain compound 1-chloro-4-iodo-2-(4-methoxybenzyl)benzene shown in formula III:

[0053]

[0054] 3) The compound shown in formula III...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses an empagliflozin intermediate preparation method, which comprises: carrying out substitution by using p-methoxybenzyl chloride and p-iodoaniline as starting raw materials to obtain a compound IV, performing diazotization and a Sandmeyer reaction to obtain a compound III, further performing demethylation under the action of boron tribromide to obtain a compound II, and finally performing condensation with (S)-3-p-toluenesulfonyloxy tetrahydrofuran to obtain the target compound I, wherein the product purity is greater than or equal to 99.0%. According to the invention, the preparation method has advantages of simple and easily available raw materials, low cost, simple operation steps, simple post-treatment and high product yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of (S)-3-(4-(5-iodo-2-chlorobenzyl)phenoxy)tetrahydrofuran, an empagliflozin intermediate, and belongs to the technical field of organic synthesis. Background technique [0002] Diabetes is a group of metabolic diseases characterized by hyperglycemia. Hyperglycemia is caused by defective insulin secretion or impaired biological action, or both. The long-term high blood sugar in diabetes leads to chronic damage and dysfunction of various tissues, especially the eyes, kidneys, heart, blood vessels, and nerves. [0003] Empagliflozin is a type 2 sodium glucose cotransporter inhibitor jointly developed by Boehringer Ingelheim and Eli Lilly and Company. SGLT-2 inhibitors are a new type of hypoglycemic drugs, mainly by inhibiting the expression of SGLT-2 in the kidney, reducing the reabsorption of glucose by the kidney, increasing the excretion of glucose in the urine, thereby reducing the plasma glucose level,...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D307/20
CPCC07D307/20
Inventor 何平勇曹钦坡黄依依斯飞月丁海东叶利
Owner ZHEJIANG HUAYI PHARMA CO LTD OF HANGZHOU HUADONG PHARMA GRP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com