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
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Problems solved by technology

[0010] In the above synthetic route, the raw material (S)-3-hydro...

Method used

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  • Empagliflozin intermediate preparation method
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  • Empagliflozin intermediate preparation method

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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...

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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

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Application Information

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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
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