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Method for preparing penicillin sulfoxide ester through continuous flow

A penicillin and sulfoxide ester technology, which is applied in the field of continuous flow preparation of penicillin sulfoxide ester, can solve the problem of low selectivity, achieve simple operation, high production capacity per unit area, and improve process economy

Pending Publication Date: 2022-04-12
SHENYANG RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction of hydrogen peroxide oxidizing sulfide to sulfoxide has the problem of low selectivity. In order to improve the selectivity, besides the need to control the amount of hydrogen peroxide added, it is more important to choose a suitable catalyst

Method used

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  • Method for preparing penicillin sulfoxide ester through continuous flow
  • Method for preparing penicillin sulfoxide ester through continuous flow
  • Method for preparing penicillin sulfoxide ester through continuous flow

Examples

Experimental program
Comparison scheme
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Embodiment

[0034] Penicillin G potassium ester synthesis:

[0035] 4L of dichloromethane, 2Kg of penicillin G potassium, 1.165Kg of p-nitrobenzyl bromide and 100g of triethylbenzyl ammonium chloride were successively added into a 10-liter glass reactor. Stir and heat up, reflux for 6-7 hours, HPLC tracking, after the reaction is completed, cool down to room temperature, add 2L of water, stir evenly, let stand for 30 minutes, and release the organic phase. The aqueous phase was extracted twice with 0.5L dichloromethane, the organic phase was combined, and the organic phase was rinsed twice with 0.5L water, and the organic phase after rinsing was set aside, and the concentration of penicillin G potassium ester was 27.66%.

[0036] Continuous flow method for preparing penicillin sulfoxide ester:

[0037] The above device was used, wherein the first reactor 101, the second reactor 102, and the third reactor 103 were purchased from Corning Reactor Technology Co., Ltd., model: Lab Reactor&LFR...

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Abstract

The invention belongs to the technical field of chemistry and chemical engineering, and particularly relates to a method for preparing penicillin sulfoxide ester through continuous flow, which comprises the following steps: mixing hydrogen peroxide and a catalyst solution to prepare an oxidant, and carrying out continuous flow oxidation reaction on the oxidant and penicillin G potassium ester, and carrying out continuous flow quenching reaction on the oxidation reaction liquid by using a sodium hydrogen sulfite aqueous solution, and carrying out post-treatment to obtain the penicillin sulfoxide ester (GESO). According to the present invention, the method has advantages of simple operation, improved safety of the reaction unit, sustainability, high unit area production capacity compared with the traditional intermittent reaction mode, environmental protection and the like, the conversion rate of the preparation method can achieve 100%, the selectivity can achieve 99%, the separation yield can achieve 96%, and the method is suitable for industrial production. The content is greater than 99.5%, and the single impurity content index reaches the original research process standard.

Description

Technical field: [0001] The invention belongs to the technical field of chemistry and chemical engineering. Specifically, it is a continuous flow method for preparing penicillin sulfoxide ester. [0002] technical background: [0003] Cephalosporin antibiotics are widely used antibiotics. As an important intermediate in the synthesis of cephalosporin antibiotics, penicillin sulfoxide (GESO) has a wide range of applications and broad market prospects. In 1963, Eli Lilly and Company of the United States used penicillin to synthesize cephalosporins, and penicillin G potassium was used as the starting material to synthesize penicillin sulfoxide through esterification and peracetic acid oxidation. In the 1980s, Japan's Shionogi Company designed an exceptional route for the synthesis of cephalosporins, and its synthesis of penicillin sulfoxide ester was the same route as Eli Lilly's. In 2011, KUMAR Rajiv and others invented a method for synthesizing penicillin sulfoxide with hyd...

Claims

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Application Information

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IPC IPC(8): C07D499/08C07D499/18C07D499/46
CPCY02P20/584
Inventor 周龙柴宝山邢久歌王云华韩涛曹贺焦佳媛王志强鄢冬茂王珂
Owner SHENYANG RES INST OF CHEM IND
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