Preparation method of 7-aminodeacetoxy cephalosporanic acid

A technology of acetoxycephalosporanic acid and phenylacetamido, which is applied in the field of preparation of 7-phenylacetylaminodesacetoxycephalosporanic acid, can solve problems such as high cost, influence on yield, difficult control of side reactions, etc., and achieve The effect of short production cycle, less discharge of three wastes and easy operation

Active Publication Date: 2012-07-18
YILI CHUANNING BIOTECH CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, this synthesis process is relatively mature, but there are still some shortcomings and deficiencies in this method. For example, the existing method needs to filter out the solid in the oxidation step and then put it into the next step after purification, which is cumbersome to operate and reduces Improve the production efficiency, but also affect the yield and increase the discharge of three wastes
In addition, the existing methods mostly use bis-trimethylsilylurea (BSU) as the carboxyl protecting group reagent, but generally need to add more than two equivalents of reagents to react, the cost is high, and the trimethylsilyl ester generated is very unstable , so that the ring expansion reaction conditions are harsh, the side reactions are difficult to control, and the yield is low

Method used

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  • Preparation method of 7-aminodeacetoxy cephalosporanic acid
  • Preparation method of 7-aminodeacetoxy cephalosporanic acid
  • Preparation method of 7-aminodeacetoxy cephalosporanic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Add 372.5g of penicillin G potassium and 1860g of toluene to the reaction flask and stir to form a suspension, add 305.5g of triphenylchloromethane and 63.3g of tetrabutylammonium bromide, heat up to 50°C for reaction, and monitor the progress of the reaction by TLC. After the reaction was completed, the temperature was lowered to about 5°C, a solution made of 104.3g potassium acetate, 1.9g acetic acid and 930g deionized water was added, and 96.9g (1.4mol) of 50% potassium acetate was added dropwise at a temperature of 0-5°C. Hydrogen peroxide and 141.6g acetic anhydride. After the dropwise addition, react at 0-5°C, and monitor the progress of the reaction by TLC. After the reaction was completed, the organic layer was separated and washed twice with 930 g of water. After the organic layer was refluxed to separate water for 2 hours, the temperature was lowered to about 80° C., and 201.2 g of a ring expansion catalyst pyridine-acetyl bromide solution in toluene with a c...

Embodiment 2

[0044] Add 1,000 g of penicillin G potassium and 5,000 g of toluene to the reaction flask and stir to form a suspension, add 780 g of triphenylchloromethane and 140 g of tetrabutylammonium bromide, heat up to 50°C for reaction, and monitor the progress of the reaction by TLC. After the reaction is completed, filter and cool the filtrate to about 5°C. After adding a solution made of 290g of potassium acetate, 3g of acetic acid and 2000g of deionized water, add 240g of 50% hydrogen peroxide and 360g of hydrogen peroxide and 360g of Acetic anhydride. After the dropwise addition, react at 0-5°C, and monitor the progress of the reaction by TLC. After the reaction was completed, the organic layer was separated and washed twice with 2000 g of water. After the organic layer was refluxed to separate water for 2 hours, the temperature was lowered to about 60° C., and 460 g of 20% ring expansion catalyst pyridine-acetyl bromide in toluene was added. After the addition was completed, th...

Embodiment 3

[0046] Add 700g of penicillin G potassium and 3500g of toluene to the reaction flask and stir to form a suspension, add 574g of triphenylchloromethane and 91g of tetrabutylammonium bromide, heat up to 60°C for reaction, and monitor the progress of the reaction by TLC. After the reaction is completed, filter, and the filtrate is cooled to about 5°C. After adding a solution made of 203g potassium acetate, 3.5g acetic acid and 2100g deionized water, 154g concentration of 50% hydrogen peroxide and 50% hydrogen peroxide and 287 g of acetic anhydride. After the dropwise addition, react at 0-5°C, and monitor the progress of the reaction by TLC. After the reaction was completed, the organic layer was separated and washed twice with 1400 g of water. After the organic layer was refluxed to separate water for 2 hours, the temperature was lowered to about 70° C., and 287 g of a ring expansion catalyst pyridine-acetyl bromide solution in toluene with a concentration of 20% was added. Aft...

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Abstract

The invention relates to a new method for preparing 7-aminodeacetoxy cephalosporanic acid. According to the method, a continuous method is adopted, penicillin G potassium is taken as an initial raw material, and the 7-aminodeacetoxy cephalosporanic acid is obtained by esterification, oxidation, loop expanding and hydrolysis. The synthesizing method has the advantages that the operation is simple and convenient, the production period is short, the three-waste discharging amount is few, the yield is higher, the cost is low and the like.

Description

technical field [0001] The invention relates to a preparation method of 7-phenylacetylaminodesacetoxycephalosporanic acid. Background technique [0002] 7-aminodesacetoxycephalosporanic acid (7-ADCA) (structure as figure 2 Shown) is one of the three major nuclei (6-APA, 7-ACA and 7-ADCA) of β-lactam antibiotics, mainly used in the synthesis of products such as cephradine, cephalexin and cefadroxil, due to its large amount , and thus the development of its synthesis process has received extensive attention. And 7-phenylacetamidodesacetoxycephalosporanic acid (structure such as image 3 Shown) is the key intermediate of synthetic 7-ADCA. [0003] At present, the synthetic methods of 7-phenylacetylaminodesacetoxycephalosporanic acid can be roughly divided into chemical method and biological fermentation method. The research and development time of the chemical method is relatively long, and the synthesis process is relatively mature, so most of the domestic use this method ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/10
Inventor 李重阳李文忠吴海龙黄耀宗曹晓红陈媛媛
Owner YILI CHUANNING BIOTECH CO
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