Method for preparing cefditoren pivoxil cephalosporins

A technology for cefditoren pivoxil and cephalosporin, which is applied in the field of preparation of cefditoren pivoxil, can solve the problems of many by-products, difficult product purification, low reaction yield, etc. Efficient effect

Active Publication Date: 2016-07-06
湖北凌晟药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to overcome the defects such as low reaction yield, many by-products and difficult product purif

Method used

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  • Method for preparing cefditoren pivoxil cephalosporins
  • Method for preparing cefditoren pivoxil cephalosporins

Examples

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Embodiment 1

[0030] A preparation method of cefditoren pivoxil, the preparation method comprising the following steps:

[0031] 1) In the presence of TMEDA and sodium phosphate, add 7-ATCA (32.3g, 100mmol) and MAEM (38.8g, 110mmol) to the reaction kettle and contact for 2 hours in 300mL THF to obtain a mixture containing ceftoren acid. Contact reaction The temperature is 12°C; wherein the molar ratio of 7-ATCA to TMEDA and sodium phosphate is 1:1.6:0.35;

[0032] 2) Keep the temperature, add TEA (15.2g, 150mmol) to the mixture containing cefditoren acid obtained in step 1), then add iodomethyl pivalate (31.5g, 130mmol) to the above mixture and stir to react , Keep the reaction for 30 minutes, pour into water after the reaction, the amount of water is twice the volume of the amount of THF in step 1), add saturated ammonium chloride solution to adjust the pH to 5.1, filter, and filter the filter cake Cefditoren pivoxil was obtained by recrystallization from methanol, and 55.6 g of white solid wa...

Embodiment 2

[0034] A preparation method of cefditoren pivoxil, the preparation method comprising the following steps:

[0035] 1) In the presence of TMEDA and sodium phosphate, 7-ATCA (32.3g, 100mmol) and MAEM (42.3g, 120mmol) were added to the reaction kettle and contacted in 300mLTHF for 2.5 hours to obtain a mixture containing ceftoren acid. Contact reaction The temperature is 15°C; among them, the molar ratio of 7-ATCA to TMEDA and sodium phosphate is 1:2:0.2;

[0036] 2) Keep the temperature, add TEA (25.3g, 250mmol) to the mixture containing cefditoren acid obtained in step 1), and then add iodomethyl pivalate (36.3g, 150mmol) to the above mixture and stir to react , Keep the reaction for 25 minutes, pour into water after the reaction, the amount of water is 3 times the volume of the amount of THF in step 1), add saturated ammonium chloride solution to adjust the pH to 5, filter, and filter the filter cake Cefditoren pivoxil was obtained by recrystallization from methanol, and 54.5 g of...

Embodiment 3

[0038] A preparation method of cefditoren pivoxil, the preparation method comprising the following steps:

[0039] 1) In the presence of TMEDA and sodium phosphate, add 7-ATCA (32.3g, 100mmol) and MAEM (37g, 105mmol) to the reaction kettle and contact for 2 hours in 300mLTHF to obtain a mixture containing ceftoren acid. The temperature is 10°C; wherein the molar ratio of 7-ATCA to TMEDA and sodium phosphate is 1:1.5:0.5;

[0040] 2) Keep the temperature, add TEA (11.1g, 110mmol) to the mixture containing ceftoren acid obtained in step 1), then add iodomethyl pivalate (31.5g, 130mmol) to the above mixture and stir to react , Keep the reaction for 30 minutes, pour into water after the reaction, the amount of water is 2.5 times the volume of the amount of THF in step 1), add saturated ammonium chloride solution to adjust the pH to 5.2, filter, and filter the filter cake Cefditoren pivoxil was obtained by recrystallization from methanol, and 53.6 g of white solid was obtained by vacuu...

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Abstract

The invention discloses a method for preparing cefditoren pivoxil cephalosporins.The method comprises the following steps that 1, on the presence of TMEDA and sodium phosphate, 7-ATCA and MAEM are subjected to a contact reaction in THF, and a mixture containing cefditore is obtained, and the contact reaction temperature ranges from 0 to 25 DEG C; 2, the temperature is kept, TEA is added to the mixture containing cefditore obtained in the step 1, then iodomethyl pivalate is added to the mixture to be stirred for reacting, the product is poured into water after the reaction is finished, a saturated ammonium chloride solution is added, the pH is adjusted to be 5 to 5.3, filtering is carried out, and a filter cake obtained through filtering is recrystallized in methyl alcohol to obtain cefditoren pivoxil cephalosporins.According to the method, separation treatment is not needed in the intermediate steps, one-pot operation is easy, cost is reduced, the yield is high, the number of by-products is small, aftertreatment is easy, and the method is especially suitable for industrial popularization.

Description

Technical field [0001] The invention belongs to the field of medicine and chemical engineering, and specifically relates to a method for preparing cefditoren pivoxil. Background technique [0002] Cefditoren Pivoxil (Cefditoren Pivoxil) is the third-generation oral cephalosporin. It was developed by Meiji Confectionery Co., Ltd. in Japan. It was launched in Japan in 1994 and launched in China in April 2001 under the trade name Meiact. , The chemical name is 2,2-dimethylpropionyloxymethyl(6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl Amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2. 0] Oct-2-ene-2-carboxylate. Cefditoren pivoxil is mainly used for the treatment of infections caused by Gram-positive bacteria and Galanz-negative bacteria, including infections caused by Streptococcus pneumoniae, Klebsiella pneumoniae, Staphylococcus aureus, Proteus etc. The therapeutic effect. [0003] There are extensive studies on the synthesis of cefdi...

Claims

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Application Information

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IPC IPC(8): C07D501/24C07D501/04
CPCC07D501/04C07D501/24
Inventor 吴兴连
Owner 湖北凌晟药业股份有限公司
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