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Method for synthesizing 3-decarbamoyl-acetyl-cefuroxime acid compound

A technology for cefuroxime acid and aminocephalosporanic acid, which is applied in the field of organic compound synthesis, can solve the problems of waste water, waste liquid, many process steps, increased cost and environmental protection pressure, etc., and achieves low cost and environmental protection pressure and simple process steps. Effect

Active Publication Date: 2021-04-20
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this type of method can obtain higher yield and purity, there are also many phenomena that are difficult to suppress in the process: many process steps, many waste water and waste liquid, and strong alkali and strong acid environment in the process. Various unfavorable factors such as product decomposition and by-product generation increase the cost of subsequent treatment and environmental protection pressure

Method used

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  • Method for synthesizing 3-decarbamoyl-acetyl-cefuroxime acid compound
  • Method for synthesizing 3-decarbamoyl-acetyl-cefuroxime acid compound

Examples

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Embodiment 1

[0039] In a 25mL reaction vessel, the weighed PdCl 2 [(tBu) 2 P(OH)] (5.0% mol) was put in, airtight, and replaced with nitrogen three times; then 2-(2-furyl)-2-oxo-acetaldehyde (1.2equiv.) and 7-aminocephalosporin Acid (0.2mmol, 1.0equiv.) was dissolved in 2-methyltetrahydrofuran (0.1M) except the water, and then, the solution was injected into a closed reaction vessel; then the weighed tert-butanol peroxide ( 2.0equiv.) into; fully stirred, and reacted at 45°C for 2.5 hours; then, the weighed pivalic acid (5.0%mol) was put into the reaction vessel, and then the weighed pivalic acid was kept at 45°C. A good 40%wt methoxyamine (2.0euqiv.) aqueous solution was slowly dripped dropwise into a closed reaction vessel for 2.5 hours; the residue of 7-aminosporanic acid was detected by high performance liquid chromatography, and the After the reaction, cool the system to room temperature; wash, extract the organic phase, and use flash column chromatography to remove the target produ...

Embodiment 2

[0042] In a 25mL reaction vessel, the weighed Pd(tBu 3 ) 2 (5.0%mol) was put in, airtight, replaced with nitrogen 3 times; then 2-(2-furyl)-2-oxo-acetaldehyde (1.2equiv.) and 7-aminocephalosporanic acid (0.2mmol, 1.0equiv.) was dissolved in 2-methyltetrahydrofuran (0.1M) except water, and then the solution was poured into a closed reaction vessel; then weighed tert-butanol peroxide (2.0equiv.) into; fully stirred, and reacted for 3 hours at 45°C; then, the weighed pivalic acid (5.0%mol) was put into the reaction vessel, and then the weighed 40%wt Methoxyamine (2.0euqiv.) aqueous solution was slowly dripped into the airtight reaction vessel drop by drop for 3 hours; the residue of 7-aminosporanic acid was detected by high performance liquid chromatography, and after the detection reaction was finished, the Cool the system to room temperature; wash, extract the organic phase, and use flash column chromatography to remove the target product. The stationary phase of the chromato...

Embodiment 3

[0044] In a 25mL reaction vessel, the weighed PdCl 2 (dppf) (10.0% mol) and iodobenzene acetate (2.5equiv.) were put in, airtight, and replaced with nitrogen for 3 times; then 2-(2-furyl)-2-oxo-acetaldehyde (1.2equiv. ) and 7-aminocephalosporanic acid (0.2mmol, 1.0equiv.) were dissolved in tetrahydrofuran (0.1M) except water, and then the solution was poured into a closed reaction vessel; fully stirred and reacted at 50°C for 3 hour; then, the weighed acetic acid (8% mol) is put into the reaction vessel, and at a temperature of 50° C., then the weighed 40% wt methoxyamine (2.5euqiv.) aqueous solution is slowly, Drop by drop into a closed reaction container for 3 hours; detect the residue of 7-aminosporanic acid by high performance liquid chromatography, after the detection reaction is completed, cool the system to room temperature; wash, extract the organic phase, and use a rapid Column chromatography goes out target product, and the stationary phase of chromatographic column...

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Abstract

The invention provides a method for synthesizing a 3-decarbamoyl-acetyl-cefuroxime acid compound. The method comprises the following steps: taking 2-(2-furyl)-2-oxo-acetaldehyde, 7-aminocephalosporanic acid and methoxyamine as raw materials; reacting the raw materials in a reaction solvent under the combined action of a first catalyst, an oxidizing agent and a second catalyst; and carrying out chromatography to obtain the 3-deaminobenzoyl acetyl cefuroxime acid compound. By using the method, the process steps are simple, the byproduct is mainly water, a large amount of other wastes do not exist, and the subsequent treatment cost and the environmental protection pressure are low.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a method for synthesizing 3-decarbamyl-acetyl-cefururoxime acid compound. Background technique [0002] Amide bonds are widely found in natural products, polymers and pharmaceuticals. Amidation reaction is a very important chemical reaction in the synthesis of natural products, materials and drug molecules containing amide bonds. The development of new synthesis methods of high atom economy and environment-friendly amide bonds is still a research content with important research significance and value in this field. From the perspective of the development of modern organic synthesis, the chemical reaction to form an amide bond is one of the most classic transitions in organic chemistry. The relatively mature synthesis route of amide compounds is the reaction of amine and carboxylic acid (or its derivatives), such as Schmit reaction, Beckmann rearrangement re...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/06
Inventor 司维森梁寒冰王辉贾开磊
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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