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Preparation method of 2-methoxyiminofurylacetic acid amonium salt

A technology of furan ammonium salt and acetylfuran, applied in directions such as organic chemistry, can solve problems such as low conversion rate of furan ketone acid, and achieve the effects of low cost, reduced side reactions and high yield

Active Publication Date: 2013-01-09
SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Further, the present invention has adopted the reaction temperature of oximation of 58~60 ℃, and the generation rate of furoic acid is less than 1%, has improved the yield of product greatly, but the conversion rate of furanonic acid is relatively low

Method used

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  • Preparation method of 2-methoxyiminofurylacetic acid amonium salt
  • Preparation method of 2-methoxyiminofurylacetic acid amonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Mix and stir 200ml of water and 30g of acetylfuran, add 0.5g of copper sulfate, then add 85ml of hydrochloric acid, control the temperature at 75~80°C, add dropwise sodium nitrite aqueous solution (80g of sodium nitrite mixed with 330ml of water), after the dropwise addition is completed , adding hydrochloric acid to adjust the pH value to 3, to obtain furanone acid solution, liquid phase detection, the conversion rate is 95.17%; the solution is mixed with 70ml methoxyammonium salt, hydrochloric acid is adjusted to pH value 2, through decolorization, extraction, crystallization, refining 33 g of furan ammonium salt product was obtained.

Embodiment 2

[0026] Mix and stir 200ml of water and 30g of acetylfuran, add 0.5g of ferric sulfate, then add 85ml of hydrochloric acid, control the temperature at 40~45°C, add dropwise sodium nitrite aqueous solution (80g of sodium nitrite mixed with 330ml of water), after the dropwise addition is completed , adding hydrochloric acid to adjust the pH value to 2, to obtain furanone acid solution, liquid phase detection, the conversion rate is 94.35%; the solution is mixed with 70ml methoxyammonium salt, hydrochloric acid is adjusted to pH value 3, through decolorization, extraction, crystallization, refining 32.6 g of furan ammonium salt product was obtained.

Embodiment 3

[0028] Mix 200ml of water and 30g of acetylfuran, stir, add 0.5g of zinc sulfate, then add 85ml of hydrochloric acid, control the temperature at 60~65°C, add dropwise sodium nitrite aqueous solution (80g of sodium nitrite mixed with 330ml of water), dropwise addition is complete Finally, add hydrochloric acid to adjust the pH value to 2 to obtain furanone acid solution, liquid phase detection, conversion rate 95.35%; Refined to obtain 33.6 g of furan ammonium salt product.

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Abstract

The invention relates to a preparation method of 2-methoxyiminofurylacetic acid amonium salt, and belongs to the technical field of medical intermediate preparation. The preparation method of the 2-methoxyiminofurylacetic acid amonium salt comprises the steps as follows: reacting acetylfuran and sodium nitrite to obtain furan ketonic acid under the catalyzing of metal salt; and then mixing the furan ketonic acid and methoxy-ammonium salt to obtain the 2-methoxyiminofurylacetic acid amonium salt. According to the preparation method provided by the invention, the transformation rate of the furan ketonic acid can be improved under the catalysis of the added metal salt, the side reaction is reduced, therefore, the yield of the 2-methoxyiminofurylacetic acid amonium salt is improved; the preparation method is simple and convenient in operation, low in cost, high in safety, and high in yield; and the quality of the prepared product meets the requirement of national standard.

Description

technical field [0001] The invention relates to a preparation method of furan ammonium salt, belonging to the technical field of preparation of pharmaceutical intermediates. Background technique [0002] Ammonium furan is one of the intermediates of the antibiotic cefuroxime widely used clinically, and its structural formula is as follows: [0003] [0004] Cefuroxime is a semi-synthetic broad-spectrum cephalosporin antibiotic for parenteral administration. Ammonium furan is one of the important intermediates of cefuroxime. [0005] Patent 200810121255 relates to the preparation method of furan ammonium salt. The method is to add 2-oxo-2-furyl acetic acid and water into the reaction vessel, adjust the pH value with inorganic acid, and then add methoxyamine aqueous solution or its hydrochloride Aqueous solution; heat preservation reaction, controlled by inorganic base and inorganic acid in the reaction process, adjusting the pH value of the reaction solution with inorgan...

Claims

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Application Information

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IPC IPC(8): C07D307/54
Inventor 郑庚修蔡会敏张治中朱冲杜涵月刘娜申德鹏
Owner SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD
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