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One-step method for the preparation of anidulungin intermediate p-amyloxy terbenzoic acid

A technology of p-pentoxy terbenzoic acid and anidulungin, which is applied in the field of preparation of p-amyloxy terbenzoic acid, an intermediate of anidylfungin, in one-step synthesis, and can solve the problems of high production risk, low production cost, High production cost and other problems, to achieve the effect of low production cost, less three wastes, and short preparation route

Active Publication Date: 2020-09-04
TIANJIN DERCHEMIST SCI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to provide a kind of raw material that is easy to get, does not have high requirements on reaction equipment, and has low production cost, short preparation route, mild reaction, easy purification, and efficiently synthesizes the p-amyloxy triplet compound of anifungin intermediate A preparation method of benzoic acid, which solves technical problems such as high production cost, high production risk, and many wastes, and is convenient for industrialized large-scale production to meet the rapidly growing commercial demand

Method used

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  • One-step method for the preparation of anidulungin intermediate p-amyloxy terbenzoic acid
  • One-step method for the preparation of anidulungin intermediate p-amyloxy terbenzoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Add 30L of N,N-dimethylformamide to the prepared potassium carbonate solution (7600g potassium carbonate + 30L water) at room temperature, and then add 2000g of 4-bromobenzoic acid and 3650g of 1,4-benzenedi Pinacol borate. The system was replaced with nitrogen for 3 times, and 100 g of tetrakis(triphenylphosphine)palladium was added as a catalyst. Under the protection of nitrogen, the temperature was slowly raised to 73°C and stirred for 7 hours. Keeping the temperature constant, 2450 g of 4-n-pentyloxybromobenzene and 5 L of dimethylformamide solution were slowly added dropwise. After 4 hours of dropping, the reaction was continued for 8 hours. After the completion of the reaction, cool to 8°C, add 0.5N dilute hydrochloric acid aqueous solution to the system dropwise under stirring until the system pH=5, and stir for 2 hours after the addition. Suction filtration, the filter cake was rinsed twice with water and once with ethanol to obtain the target product anifungin...

Embodiment 2

[0034] Add 40L of N,N-dimethylformamide to the prepared sodium carbonate solution (5000g sodium carbonate + 25L water) at room temperature, and then add 1600g of 4-bromobenzoic acid and 3000g of 1,4-benzenedi Pinacol borate. The system was replaced with nitrogen for 3 times, and 95 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride was added as a catalyst. Under the protection of nitrogen, the temperature was slowly raised to 76°C and stirred for 7 hours. Keeping the temperature constant, 1950 g of 4-n-pentyloxybromobenzene and 4.7 L of dimethylformamide solution were slowly added dropwise. After 3.5 hours of completion of the dropwise addition, the reaction was continued for 8 hours. After the reaction was completed, cool to 8° C. with a water bath, add 0.5 M dilute hydrochloric acid aqueous solution to the system dropwise with stirring until the system pH=4, and stir for 2 h after the addition. Suction filtration, the filter cake was rinsed twice with water and...

Embodiment 3

[0036] Add 20L of N,N-dimethylformamide to the prepared cesium carbonate solution (8600g cesium carbonate + 20L water) at room temperature, and then add 1000g of 4-bromobenzoic acid and 1800g of 1,4-benzenedi Pinacol borate. The system was replaced with nitrogen for 3 times, and 40 g of palladium acetate was added as a catalyst. Under the protection of nitrogen, the temperature was slowly raised to 75°C and stirred for 7 hours. Keeping the temperature constant, 1220 g of 4-n-pentyloxybromobenzene and 3 L of dimethylformamide solution were slowly added dropwise. After 2 hours of dropwise addition, the reaction was continued for 8 hours. After the reaction was completed, cool to 6° C. with a water bath, add 0.5 M dilute hydrochloric acid aqueous solution to the system dropwise with stirring until the system pH=5, and stir for 2 h after the addition. Suction filtration, the filter cake was rinsed twice with water and once with ethanol to obtain the target product anifungin inter...

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Abstract

The invention belongs to the field of compound preparation and discloses a preparation method for synthesizing an anidulafungin intermittent ([1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-) through a one-step method. The method comprises the following steps: under a condition of an alkali solution, by taking N,N-dimethyl formamide as a solvent, catalyzing with a palladium catalyst, adding 4-bromobenzoic acid, 1,4-phenylenediboronic acid pinacol ester and 4-(n-pentyloxy) bromobenzene as raw materials, and performing an SUZUKI coupling reaction, thereby obtaining a target product, namely the anidulafungin intermittent ([1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-). The raw materials used in the method are all industrial products available in the market, the raw materials are easily available, in addition, the steps are simple, the reaction conditions can be controlled, wastes are greatly reduced in the production process of the product, and chemical environmental-friendly requirements of the current society are met.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to a preparation method for synthesizing anidifungin intermediate p-amyloxy terbenzoic acid by one-step method. Background technique [0002] The p-amyloxy terbenzoic acid prepared by the invention is a key intermediate of anidungin medicine, which is very important for the industrialized production of anidungin. Wherein the structure of Anifungin is: [0003] [0004] Anidifungin is an echinocandin antifungal drug indicated for the treatment of candidemia, other types of candida infections (abdominal abscesses, peritonitis) and esophageal candida infections in adults. The drug was developed and marketed by Pfizer. It was first approved by the US Food and Drug Administration (FDA) on February 17, 2006, and then approved by the European Medicines Agency (EMA) on September 20, 2007. , marketed by Pfizer in the United States and Europe under the trade name The glo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/353C07C51/367C07C65/24
CPCC07C51/353C07C51/367C07C65/24
Inventor 张术兵谢延民杨洪波王海涛
Owner TIANJIN DERCHEMIST SCI TECH
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