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Novel synthesis method of cefprozil

A technology of cefprozil and a new method, which is applied in the field of new cefprozil synthesis and preparation, can solve the problems of low yield of cefprozil, achieve mild and easy control of reaction conditions, good practical value and significance of production promotion and application, and simple process route Effect

Inactive Publication Date: 2018-08-24
TOPFOND PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of this application is to provide a new synthetic method for cefprozil, which can partially solve the defect of low yield in the existing cefprozil preparation process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthetic method of cefprozil provided in this embodiment, the concrete steps are described as follows.

[0029] (1) Base substitution reaction

[0030] Using dichloromethane as an aprotic solvent, add 95ml of dichloromethane into a dry reactor, and add β-lactam nucleus 7-amino-3-(Z-prop-1enyl)-4-cephalosporin Acid 10g, under the condition of -30℃, slowly drop 6.4g of sterically hindered ammonia non-nucleophilic base 1,8-diazabicycloundecene-7-ene, carry out base substitution reaction, stir the reaction until dissolved until.

[0031] (2) Condensation reaction

[0032] Keep the condition at -30°C, slowly add 14.2ml of branched chain D-p-hydroxyphenylglycine derivative p-hydroxyphenylglycine ethylene glycol ester dropwise to the solution obtained in step (1), after the reaction is complete (no residue detected by HPLC) (It takes about 4 hours), add 5mol HCL to extract, pass NH 3 Adjust the pH to about 5.0 to precipitate crystals, filter the crystals and dry them ...

Embodiment 2

[0034] The preparation method of Cefprozil provided by the present embodiment is the same as that of Example 1, and only some parameters are adjusted as follows:

[0035] In step (1), the large hindered ammonia non-nucleophilic base was adjusted to lithium diisopropylamide, and the dosage was 4.7 g; finally about 13.2 g of cefprozil finished product was obtained (the calculation showed that the molar yield was 67.42%).

Embodiment 3

[0037] The preparation method of Cefprozil provided by the present embodiment is the same as that of Example 1, and only some parameters are adjusted as follows:

[0038] In step (1), the large sterically hindered ammonia non-nucleophilic base is adjusted to N,N-diisopropylethylamine, and the dosage is 5.4g;

[0039] In step (2), triethylamine was used to adjust the pH to about 5.0 to precipitate crystals, and finally about 13.2 g of cefprozil finished product was obtained (the calculation showed that the molar yield was 67.42%).

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Abstract

The invention belongs to the technical field of medicine synthesis and preparation and in particular relates to patent application of a novel cefprozil synthesis and preparation method. The method hasthe technical thought as follows: alkali substitution reaction is carried out on beta-lactam parent nucleus(7-amin-3-(Z-prop-1-enyl)-4-cephalosporanic acid) in an aprotic solvent; then a branched-chain D-p-hydroxyphenylglycine derivative is added to carry out condensation reaction, so that cefprozil is prepared. Totally, the preparation method provided by the invention has the advantages of easiness for obtaining reaction raw materials, moderate reaction conditions and easiness for controlling; after the reaction is finished, the residue of main raw materials is relatively low, the cost pressure caused by the main raw materials can be greatly reduced and the yield of the cefprozil is relatively high; meanwhile, the method has a relatively simple process route and a high-quality cefprozilproduct can be obtained through two-step reaction; the defects of an existing cefprozil preparation method that the yield is relatively low and the quality is not stable can be totally overcome relatively well; the method has relatively good practical value and production and popularization application meaning.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and preparation, and specifically relates to a patent application for a new synthesis and preparation method of cefprozil. Background technique [0002] Cefprozil (Cefprozil), chemical name: (6R,7R)-7[(R)-2-amino-2-(p-hydroxy-phenyl)acetamido]-8-oxo-3-propene-5- Thia-1-azabicyclo-(4,2,0)oct-2-ene-2carboxylic acid-hydrate, molecular formula: C 18 h 19 N 3 o 5 S·H 2 O. Cefprozil is a second-generation cephalosporin antibiotic with a broad-spectrum antibacterial effect and has a good safety advantage in the children's drug market, so it is widely used. [0003] The existing preparation process route of cefprozil is mainly: p-hydroxyphenylglycine Deng potassium salt and pivaloyl chloride generate Deng potassium hydrochloric anhydride, and then combine with 7-amino-3-(Z-prop-1-enyl)-4-cephalosporin Acid reaction to generate 7-[2-butenoic acid methyl ester-amino-2-(p-hydroxy-phenyl)acetami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/06
CPCC07D501/06C07D501/22
Inventor 吴明书王俊臣杨明钱丹杨秋燕张春生任真陈金春年蓓蕾武妍杰程亚丽
Owner TOPFOND PHARMA CO LTD
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