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Novel synthesis process for 5-amino-1-hydroxyethyl pyrazole or the like

A technology for hydroxyethylpyrazole and its analogues, which is applied in the field of new synthesis technology of 5-amino-1-hydroxyethylpyrazole and its analogues, and can solve the problem of the high price of cefotaxime sulfate and the impact on market sales and popularization, high production costs and other issues, to achieve the effect of low cost, easy operation and cheap reagents

Inactive Publication Date: 2009-02-18
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method route is shorter, because 3-methoxy acrylonitrile or 3-methoxy-2-nitrile base-acrylonitrile or 3-methoxy-2-acetic acid oxymethyl-acrylonitrile etc. are expensive, And difficult to obtain, cause the production cost height of 5-amino-1-hydroxyethylpyrazole, also cause the cefotaxime sulfate price to remain high, have had a strong impact on its marketing and promotion

Method used

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  • Novel synthesis process for 5-amino-1-hydroxyethyl pyrazole or the like
  • Novel synthesis process for 5-amino-1-hydroxyethyl pyrazole or the like
  • Novel synthesis process for 5-amino-1-hydroxyethyl pyrazole or the like

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Embodiment 1

[0016] The synthesis of embodiment 1,5-amino-1-hydroxyethylpyrazole:

[0017] (1), the synthesis of β-hydroxyethylhydrazine

[0018] 32.0 grams of sodium hydroxide and 200.0 grams of 80% hydrazine hydrate were mixed together and stirred evenly, stirred at room temperature for 30 minutes, stirred at 70°C for 2.5 hours, cooled in an ice bath, added 64.4 grams of chloroethanol dropwise, and kept the temperature at 30 React at ~45°C for 2 hours, concentrate the reaction solution, remove solid sodium chloride by filtration, rinse the filter cake with ethyl acetate, and collect fractions at 127°C / 2.27KPa under reduced pressure. 1 H NMR: 2.64(t, 2H), 3.45(t, 2H), 3.67(br, 4H);

[0019] (2), the synthesis of 5-amino-1-hydroxyethyl-5-pyrazoline

[0020] Add dropwise a mixed solution of 53 g of acrylonitrile and 400 mL of toluene to 76.0 g of the above product, stir and react at 95-100°C for 8 hours, concentrate under reduced pressure, refrigerate to precipitate crystals, filter, rins...

Embodiment 2

[0025] The synthesis of embodiment 2,5-amino-1-hydroxyethylpyrazole analogue:

[0026] (1), the synthesis of β-hydroxypropylhydrazine

[0027] Mix 32.0 grams of sodium hydroxide and 200.0 grams of 80% hydrazine hydrate together and stir evenly, stir at room temperature for 30 minutes, stir at 70°C for 2.5 hours, cool in an ice bath, add 75.7 grams of chloropropanol dropwise, and after the dropwise addition, keep the temperature React at 40-55°C for 2.5 hours, concentrate the reaction solution, filter to remove solid sodium chloride, rinse the filter cake with ethyl acetate, and collect fractions under reduced pressure;

[0028] (2), the synthesis of 5-amino-1-hydroxypropyl-5-pyrazoline

[0029] Add dropwise a mixed solution of 53 g of acrylonitrile and 400 mL of toluene to 90.0 g of the above product, stir and react at 100-110°C for 8.5 hours, concentrate under reduced pressure, refrigerate to precipitate crystals, filter, rinse the filter cake with ice ethanol, and dry. The...

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Abstract

The present invention discloses a novel synthesis process of 5-amino-1-ethylol pyrazole and analog compounds thereof. In the process, acrylonitrile is used as a raw material, and the 5-amino-1-ethylol pyrazole and the analog compounds are synthesizsed through a certain process. The present invention has the advantages that the agents are cheap, the route of the synthesis process is simple, the operation is simple, the yield of synthesis is high, and the cost is low.

Description

field of invention [0001] The invention relates to a new synthesis process of the C-3 side chain 5-amino-1-hydroxyethylpyrazole of the fourth-generation cephalosporin antibiotic cefotaxime sulfate and its analogues. Background of the invention [0002] 5-amino-1-hydroxyethylpyrazole is the C-3 side chain of the fourth generation cephalosporin antibiotic cefotaxime sulfate (Cefoselis sulfate), its introduction has expanded the antibacterial spectrum of cefotaxime sulfate, enhanced Improve antibacterial activity, especially enhance the antibacterial activity against Pseudomonas aeruginosa, so that it has high antibacterial activity against Gram-positive bacteria and negative bacteria. At present, the excellent antibacterial effect of the drug in vitro and in animal infection models has been confirmed by a large number of clinical experiment reports worldwide. It has been successfully applied at home and abroad: (1) surgical infection, (2) respiratory tract infection; (3) obst...

Claims

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Application Information

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IPC IPC(8): C07D231/38
Inventor 黄朋勉杨道武徐玲敏王俊陈平
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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