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Method for synthesizing (z)‑2‑(α‑methoxyimine) ammonium furoacetate

A technology of ammonium furanacetate and methoxyimine, applied in organic chemistry methods, organic chemistry, etc., can solve the problems of difficult product refinement, unfavorable production, increased cost, etc., achieve high yield, good product quality, and reduce resources wasteful effect

Active Publication Date: 2017-11-07
SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the influence of thermodynamics or kinetics, in the process of synthesizing (Z)-2-(α-methoxyimine) furan acetic acid, the proportion of by-product (E)-2-(α-methoxyimine) furan acetic acid It accounts for about 15%, resulting in a waste of raw materials. At the same time, the resulting products are not easy to refine, which will increase a lot of cost and is not conducive to production
[0003] The current production of furan ammonium salt has many process improvements, but there is no relevant literature report on the source of the control of trans generation, which determines the quality and yield of the produced product

Method used

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  • Method for synthesizing (z)‑2‑(α‑methoxyimine) ammonium furoacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Dissolve 40g of 2-oxo-2-furyl acetic acid and 0.04g of copper sulfate pentahydrate in 300mL of water, add 100g of methoxyamine aqueous solution at 0°C, and adjust the pH to 3.5 with dilute sulfuric acid;

[0027] The massfraction of described methoxyamine aqueous solution is 17%;

[0028] (2) Insulate the solution prepared in step (1) at 8°C for 4.5h to obtain 2-(α-methoxyimine)furan acetic acid solution; liquid phase detection, (Z)-2-(α-methoxy Imine)furanacetic acid: (E)-2-(α-methoxyimine)furanacetic acid is 95.1:4.9;

[0029] (3) Use dilute sulfuric acid to adjust the pH of the 2-(α-methoxyimino)furan acetic acid solution to 0.8, control the temperature to 20°C, extract with dichloromethane, and combine the organic phases;

[0030] (4) Ammonia gas was introduced into the organic phase at 5°C, the pH was adjusted to 7.0, and the crude product was obtained after heat preservation for 1 hour. After decolorization, concentration and crystallization, 48.9 g of the pr...

Embodiment 2

[0038] (1) Dissolve 40g of 2-oxo-2-furylacetic acid and 0.032g of manganese dichloride in 300mL of water, add 160g of methoxyamine hydrochloride aqueous solution at 5°C, and adjust the pH to 3.0 with potassium hydroxide;

[0039] The massfraction of described methoxyamine hydrochloride aqueous solution is 20%;

[0040] (2) Insulate the solution prepared in step (1) at 10°C for 2 hours to obtain 2-(α-methoxyimine)furan acetic acid solution; liquid phase detection, (Z)-2-(α-methoxyimine) Amine) furan acetic acid: (E)-2-(α-methoxyimine) furan acetic acid is 95.0:5.0;

[0041] (3) Use dilute hydrochloric acid to adjust the pH of the 2-(α-methoxyimino)furan acetic acid solution to 0.1, control the temperature to 25° C., extract with dichloromethane, and combine the organic phases;

[0042] (4) Ammonia gas was introduced into the organic phase at 0°C, the pH was adjusted to 7.5, and the crude product was obtained after heat preservation for 1.5 h. After decolorization, concentratio...

Embodiment 3

[0050] (1) Dissolve 40g of 2-oxo-2-furyl acetic acid and 0.048g of zinc sulfate in 300mL of water, add 392g of methoxyamine aqueous solution at 10°C, and adjust the pH to 2.5 with dilute sulfuric acid;

[0051] The massfraction of described methoxyamine aqueous solution is 5%;

[0052] (2) The solution prepared in step (1) was incubated at 5° C. for 7 hours to obtain a 2-(α-methoxyimine) furan acetic acid solution; liquid phase detection (Z)-2-(α-methoxyimine ) furan acetic acid: (E)-2-(α-methoxyimine) furan acetic acid is 95.5:4.5,

[0053] (3) Use dilute phosphoric acid to adjust the pH of the 2-(α-methoxyimino)furan acetic acid solution to 1.5, control the temperature to 15°C, extract with dichloromethane, and combine the organic phases;

[0054] (4) Pass liquid ammonia into the organic phase at 10° C., adjust the pH to 6.5, and keep warm for 0.5 h to obtain the crude product. After decolorization, concentration and crystallization, 48.0 g of the product is obtained with a...

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Abstract

The invention belongs to the technical field of medical intermediate preparation, and particularly relates to a method for synthesizing (Z)-2-(alpha-methoxyimino)furanylacetic acid ammonium. The method comprises the following steps that 1, 2-oxo-2-furanylacetic acid and heavy metal salt are dissolved in water, an aqueous methoxyamine solution or aqueous methoxyamine salt solution is added at the temperature of 0 DEG C-10 DEG C, and the pH is regulated to 2.5-3.5; 2, heat preservation is performed for 2-7 h at the temperature of 5 DEG C-10 DEG C, and a 2-(alpha-methoxyimino)furanylacetic acid solution is obtained; 3, the pH of the 2-(alpha-methoxyimino)furanylacetic acid solution is regulated to 0.1-1.5 by adopting inorganic acid, the temperature is controlled at 15 DEG C-25 DEG C, extraction is performed through organic solvent, and organic phases are combined; 4, ammonia gas or liquid ammonia is introduced into the organic phases at the temperature of 0 DEG C-10 DEG C, the pH is regulated to 6.5-7.5, heat preservation is performed for 0.5-1.5 h to obtain a crude product, and after decoloration, concentration and crystallization are performed, the product is obtained. The method is high in yield and good in product quality.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, and in particular relates to a method for synthesizing (Z)-2-(α-methoxyimine)ammonium furanacetate. Background technique [0002] (Z)-2-(α-methoxyimine) ammonium furan acetate or 2-(Z)-methoxyimine-2-furan ammonium acetate, also known as furan ammonium salt, is used in the synthesis of cefuroxime axetil key intermediates. Due to the influence of thermodynamics or kinetics, in the process of synthesizing (Z)-2-(α-methoxyimine) furan acetic acid, the proportion of by-product (E)-2-(α-methoxyimine) furan acetic acid Accounting for about 15%, the waste of raw materials is caused, and the products generated are not easy to be refined, which will increase a large amount of cost and is not conducive to production. [0003] There are many technological improvements in the production of furan ammonium salts, but there is no relevant literature report on the control of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/54
CPCC07B2200/09C07D307/54
Inventor 杨兆钰张蕾孙铭叶德坤
Owner SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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