Method for synthesizing alpha-hydroxy amide compound

A synthetic method, the technology of hydroxyamide, applied in the field of organic chemical synthesis, can solve the problems of difficult control, many reaction steps, low temperature, etc., and achieve the effect of easy operation control, high reaction efficiency and appropriate temperature

Active Publication Date: 2014-04-30
杭州禾泰健宇生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0031] However, this reaction uses more complicated raw materials, and its preparation is more complicated and the requirements are higher, which makes the synthesis process more cumbersome, and the reaction needs to be completed in two steps, and its yield is not high
[0032] In summary, in the existing synthetic methods of α-hydroxyamides, the raw materials are difficult to obtain, the reaction often requires lower temperature, is difficult to control, the catalyst is relatively complicated or expensive, and the reaction steps are many, often accompanied by side reactions, resulting in low rate

Method used

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  • Method for synthesizing alpha-hydroxy amide compound
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  • Method for synthesizing alpha-hydroxy amide compound

Examples

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Effect test

Embodiment 1

[0075] The synthetic method of 2-(2-bromophenyl)-2-hydroxyl-N-phenylacetamide specifically comprises the following steps:

[0076] (1) Add 0.3 grams of 2-(2-bromophenyl)-N-phenylacetamide, 0.15 grams of potassium hydroxide, and 10 milliliters of dimethyl sulfoxide to a 50-ml two-necked flask, and in air atmosphere Seal the tube and stir it magnetically at 50°C for 24 hours;

[0077] (2) After the reaction, cool to room temperature, add saturated brine to wash, extract 3 times with ethyl acetate, combine the organic layers, dry over anhydrous sodium sulfate, and concentrate under reduced pressure with a rotary evaporator to remove the solvent in the solution to obtain crude product;

[0078] (3) The crude product was separated and purified by 300-400 mesh silica gel column chromatography (volume ratio of petroleum ether: ethyl acetate = 4:1) to obtain a white solid, namely 2-(2-bromophenyl)-2-hydroxy -N-phenylacetamide, yield 81%, melting point: 140-141°C.

[0079] The resul...

Embodiment 2

[0084] The synthetic method of 2-(2-bromophenyl)-2-hydroxyl-N-(4-methylphenyl)acetamide specifically comprises the following steps:

[0085] (1) Add 3.2 grams of 2-(2-bromophenyl)-N-(4-methylphenyl)acetamide, 1.6 grams of potassium hydroxide, and 100 milliliters of dimethyl Sulfone, sealed in air atmosphere, and magnetically stirred at 50°C for 24 hours;

[0086] (2) After the reaction, cool to room temperature, add saturated brine to wash, extract 4 times with ethyl acetate, combine the organic layers, dry over anhydrous sodium sulfate, and concentrate under reduced pressure with a rotary evaporator to remove the solvent in the solution to obtain crude product;

[0087] (3) The crude product was separated and purified by 300-400 mesh silica gel column chromatography (volume ratio of petroleum ether: ethyl acetate = 4:1) to obtain a white solid, namely 2-(2-bromophenyl)-2-hydroxy -N-(4-methylphenyl)acetamide, the yield is 84%, melting point: 148-149°C.

[0088] The resultin...

Embodiment 3

[0093] The synthetic method of 2-(2-bromophenyl)-2-hydroxyl-N-(4-ethoxyphenyl) acetamide specifically comprises the following steps:

[0094] (1) Add 3.5 grams of 2-(2-bromophenyl)-N-(4-ethoxyphenyl)acetamide, 1.5 grams of potassium hydroxide, and 80 milliliters of dimethylmethylene to a 250-ml two-necked flask. Sulfone, sealed in air atmosphere, and magnetically stirred at 50°C for 24 hours;

[0095] (2) After the reaction, cool to room temperature, add saturated brine to wash, extract 5 times with ethyl acetate, combine the organic layers, dry over anhydrous sodium sulfate, and concentrate under reduced pressure with a rotary evaporator to remove the solvent in the solution to obtain crude product;

[0096] (3) The crude product was separated and purified by 300-400 mesh silica gel column chromatography (volume ratio of petroleum ether: ethyl acetate = 5:1) to obtain a white solid, namely 2-(2-bromophenyl)-2-hydroxy -N-(4-ethoxyphenyl)acetamide, yield 80%, melting point: 1...

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Abstract

The invention provides a method for synthesizing an alpha-hydroxy amide compound. The method specifically comprises the following steps: (1) mixing amide, an alkali and dimethyl sulfoxide, sealing in an air atmosphere, and reacting; (2) cooling to room temperature after the reaction is ended, adding saturated salt water for washing, extracting for 3-5 times by using ethyl acetate, merging an organic layer, drying through anhydrous sodium sulfate, performing vacuum concentration, and obtaining a crude product; and (3) purifying the crude product through chromatographic separation, and obtaining the needed alpha-hydroxy amide compound. Compared with the prior art, the method is performed in a simple potassium hydroxide/dimethyl sulfoxide system, and a complex or expensive catalyst is avoided; the raw materials are easily prepared; the temperature is proper, and the operation is easily controlled; a target product is directly obtained in one step by taking air as a green oxidant; the reaction is high-efficiency, the yield is 98 percent, and industrial production is promoted.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for synthesizing α-hydroxyamide compounds. Background technique [0002] α-Hydroxyamides have unique pharmacological and physiological activities and play an important role in organic chemistry and medicinal chemistry. These compounds have antiviral, bactericidal and antitumor activities, and are often used as inhibitors of various enzymes and antibodies. This molecular skeleton is contained in some natural products such as sea anemones and marine cyanobacteria. It is also a very important synthetic intermediate. FK-156 produced by Strepto myces olivacegriseus and Streptomyces violaceus has a skeleton structure of α-hydroxyamide. On the one hand, FK-156 can be used as an immune enhancer to prevent bacterial infection, and on the other hand, it can be used for protein synthesis. And α-hydroxyamide compounds also occupy an important position in the field of org...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/38C07C231/12
Inventor 张武郭玉军刘亮王飞
Owner 杭州禾泰健宇生物科技有限公司
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