Preparation method of aminothiazole acetyloxime acid with controllable particle size

A technology of aminothiazole acetoxamic acid and ethyl desmethylaminothiazole acetoxamic acid, which is applied in the field of preparation of aminothiazole acetoxamic acid with controllable particle size, can solve problems such as difficult control of intermediate products, and achieve controllable particle size and simple process operation Effect

Inactive Publication Date: 2021-04-13
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is difficult to control the relevant indicators of intermediate products in the process of esterification

Method used

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  • Preparation method of aminothiazole acetyloxime acid with controllable particle size
  • Preparation method of aminothiazole acetyloxime acid with controllable particle size
  • Preparation method of aminothiazole acetyloxime acid with controllable particle size

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Hydrolysis process: 50.00 g of ethyl demethylaminothiaxate, 150 ml of tap water and 50 ml of methanol were placed in a 500 ml three-neck flask, and 27.00 g of sodium hydroxide was added to the system at room temperature, and stirred overnight after dropping to obtain compound 1.

[0040] Acylation process: 97.0 g of acetic anhydride was added dropwise to the system, and stirred for 4 hours after dropping to obtain compound 2.

[0041] Crystallization process: Add 1100ml of tap water and 2g of activated carbon for decolorization, maintain the system temperature at 10-15°C, add 20wt.% hydrochloric acid aqueous solution dropwise to pH = 3-4, and control the dropwise addition for 45min. Suction filtration, washing with 50 ml of water three times respectively, to obtain the wet product of compound 3, and drying in vacuum to obtain 135.28 g of the dry product of compound 3, with a yield of 78.5%. Particle size detection showed that its D50% particle size was 57.559 μm.

Embodiment 2

[0043] Hydrolysis process: 50.00 g of ethyl demethylaminothiaxate, 150 ml of tap water and 50 ml of methanol were placed in a 500 ml three-necked flask, and 27.01 g of sodium hydroxide was added to the system at room temperature, and stirred overnight after dropping to obtain compound 1.

[0044] Acylation process: 97.0 g of acetic anhydride was added dropwise to the system, and stirred for 4 hours after dropping to obtain compound 2.

[0045] Crystallization process: Add 1100ml of tap water and 2g of activated carbon for decolorization, maintain the system temperature at 10-15°C, add 20wt.% hydrochloric acid aqueous solution dropwise to pH = 3-4, and control the dropwise addition for 45min. Suction filtration, washing with 50 ml of water three times respectively to obtain the wet product of Compound 3, and drying in vacuum to obtain 132.69 g of the dry product of Compound 3, with a yield of 77.0%. Particle size detection showed that its D50% particle size was 67.902 μm.

Embodiment 3

[0047] Hydrolysis process: 50.00 g of ethyl demethylthiaxamate, 150 ml of water, 30 ml of tetrahydrofuran, 192.40 g of potassium carbonate were added to the system at room temperature, and the mixture was stirred overnight to obtain compound 1.

[0048] Acylation process: 97.0 g of acetic anhydride was added dropwise to the system, and stirred for 4 hours after dropping to obtain compound 2.

[0049] Crystallization process: Add 1100ml of tap water and 2g of activated carbon for decolorization, maintain the system temperature at 20-25°C, add 30wt.% acetic acid aqueous solution dropwise to pH = 3-4, and add dropwise for 45min at a controlled time. Suction filtration and rinsing with 50ml of water three times respectively to obtain the wet product of Compound 3, which was dried in vacuum to obtain 119.42 g of the dry product of Compound 3 with a yield of 73.5%. Particle size detection showed that its D50% particle size was 76.004 μm.

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Abstract

The invention relates to a preparation method of aminothiazole acetyloxime acid with a controllable particle size, and belongs to the technical field of chemical pharmacy. The preparation method comprises the following steps: ahydrolysis step: hydrolyzing ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetate serving as a raw material to generate a compound 1; an acylation step: dropwisely adding an acylating agent into the system to perform acylation reaction to obtain a compound 2; and a crystallization step: adding activated carbon into the reaction system for decolorization, then dropwise adding an acidic solution into the system at different temperatures to control the pH value of the system, and after the solid is separated out, carrying out centrifugal drying to obtain a compound 3 with controllable particle size. According to the method, by controlling different acid liquor adding temperatures, the particle size of the prepared aminothiazole acetyloxime acid is controllable; and the technological process is simple to operate and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of aminothiazole acetoxamic acid with controllable particle size, which belongs to the technical field of chemical pharmacy. Background technique [0002] Aminothiazole acetoxamic acid, chemical name: (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminoacetic acid CAS: 110130-88-6 Molecular weight: 229.21300 Molecular formula: C 7 h 7 N 3 o 4 The molecular structure of S is: [0003] [0004] Aminothiazole acetoxamic acid is an intermediate product of cefdinir active thioester, and the control of its production process and related quality standards is critical to the quality of cefdinir active thioester. Cefdinir is an excellent third-generation oral cephalosporin antibiotic. It is clinically used to treat infectious diseases caused by sensitive bacteria. It has broad-spectrum antibacterial activity, high safety, few side effects, and good clinical application effect. It belongs to the domestic and foreign m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/593
CPCC07D277/593
Inventor 余成刘承平彭亮王雅琦
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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