Method for synthesizing (Z)-2-(alpha-methoxyimino)furanylacetic acid ammonium

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: 2016-04-20
SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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  • Abstract
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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 t

Method used

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  • Method for synthesizing (Z)-2-(alpha-methoxyimino)furanylacetic acid ammonium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0027] The mass fraction of the methoxyamine aqueous solution is 17%;

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

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

[0030] (4) Ammonia gas was passed 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 product was obtained, and t...

Embodiment 2

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

[0039] The mass fraction of the methoxyamine hydrochloride aqueous solution is 20%;

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

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

[0042] (4) Ammonia gas was passed 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 hours. After decolorization, concentration and crystallization, 47.4 g of...

Embodiment 3

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

[0051] The mass fraction of the methoxyamine aqueous solution is 5%;

[0052] (2) Incubate the solution prepared in step (1) 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) Adjust the pH of the 2-(α-methoxyimine) furan acetic acid solution to 1.5 with dilute phosphoric acid, control the temperature at 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 the crude product for 0.5h. After decolorization, concentration and crystallization, the product is 48.0g, and the yield is 90%.

[0055] Product test results:

[0056] Appearance: o...

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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 specifically relates to a method for synthesizing (Z)-2-(α-methoxyimine)furan ammonium acetate. Background technique [0002] (Z)-2-(α-Methoxyimine) ammonium furan acetate or 2-(Z)-methoxyimine-2-ammonium furan acetate, also known as furan ammonium salt, is used in the synthesis of cefuroxime axetil Key intermediate. Due to the influence of thermodynamics or kinetics, in the process of synthesizing (Z)-2-(α-methoxyimine)furan acetic acid, the ratio 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 product is not easy to refine, which will increase a lot of cost and is not conducive to production. [0003] There are many technological improvements in the current production of furan ammonium salt, but there is no relevant literature report on the control of the so...

Claims

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Application Information

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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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