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Method for preparing thiazoline enol ester

A technology of thiazoline enol ester and thiazoline, which is applied in the field of preparation of thiazoline enol ester, can solve the problems of harsh conditions, high energy consumption, and low yield, and achieve low cost, high yield, and simple operation Effect

Active Publication Date: 2016-07-20
浙江沙星科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, the synthetic route of thiazoline enol ester has only been announced by Shionogi Company, but ozone is used in the process, and it needs to be reacted at ultra-low temperature, the energy consumption is high, and it is easy to form poly ozonide, which may cause The danger of explosion, strict requirements on equipment, harsh conditions, low yield, only 76.1%

Method used

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  • Method for preparing thiazoline enol ester
  • Method for preparing thiazoline enol ester
  • Method for preparing thiazoline enol ester

Examples

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Effect test

Embodiment 1

[0025] A kind of preparation method of thiazoline enol ester, specifically comprises the steps:

[0026] ① Preparation of penicillin sulfoxide ester: Add 18.6g of penicillin G potassium salt, 28mL of N,N-dimethylformamide (DMF), 100mL of dichloromethane, 9.4g of p-methoxybenzyl chloride, four Butylammonium bromide 0.56g, heated to reflux for 6 hours, monitored by TLC, cooled to 0°C, under nitrogen protection, then added 200mL of dichloromethane, then added dropwise 7.6g of 35% hydrogen peroxide, after the dropwise addition, stirred for 30 minutes , then add 1.6 g of maleic anhydride, TLC monitoring, the reaction is complete, control the temperature below 10 ° C, dropwise add 7% sodium sulfite solution, use starch-potassium iodide test paper to test that the feed liquid does not change color, and it is the end point of the dropwise addition. After the dropwise addition is completed, stir for 15 Minutes, standing for layering, the organic phase was washed with 50mL of 5% sodium ...

Embodiment 2

[0030] A kind of preparation method of thiazoline enol ester, specifically comprises the steps: 1. the preparation of penicillin sulfoxide ester: in reactor, add penicillin G potassium salt 18.6g, N,N-dimethylformamide (DMF) 28mL, Dichloromethane 100mL, p-methoxybenzyl chloride 9.4g, tetrabutylammonium bromide 0.56g, heating to reflux for 6 hours, TLC monitoring, cooling to 0°C, under nitrogen protection, then adding 200mL of dichloromethane, then drop Add 7.6g of 35% hydrogen peroxide, after the dropwise addition, stir for 30 minutes, then add 1.6g of maleic anhydride, monitor by TLC, after the reaction is complete, control the temperature below 10°C, add 7% sodium sulfite solution dropwise, and test with starch-potassium iodide test paper The feed liquid does not change color and is the end point of the dropwise addition. After the dropwise addition is completed, stir for 15 minutes, let stand and separate layers, wash the organic phase with 50mL of 5% sodium bicarbonate solu...

Embodiment 3

[0034] A kind of preparation method of thiazoline enol ester, specifically comprises the following steps: 1. the preparation of penicillin sulfoxide ester: in reactor, add penicillin G potassium salt 18.6g, N,N-dimethylformamide (DMF) 50mL, Dichloromethane 100mL, p-methoxybenzyl chloride 7.9g, tetrabutylammonium bromide 0.37g, heating to reflux for 6 hours, TLC monitoring, cooling to 0 ° C, under nitrogen protection, then adding 200mL of dichloromethane, and then drop Add 6.6g of 35% hydrogen peroxide, after the dropwise addition, stir for 30 minutes, then add 1.6g of maleic anhydride, monitor by TLC, after the reaction is complete, control the temperature below 10°C, add 7% sodium sulfite solution dropwise, and test with starch-potassium iodide test paper The feed liquid does not change color and is the end point of the dropwise addition. After the dropwise addition is completed, stir for 15 minutes, let stand and separate layers, wash the organic phase with 50mL of 5% sodium ...

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Abstract

The invention discloses a method for preparing thiazoline enol ester, and belongs to the field of synthesis of compounds. Penicillin G sylvite is adopted as a raw material, and the method comprises the following steps that 1, penicillin G sylvite is adopted as the raw material, esterification and oxidizing are carried out, and penicillin sulfoxide ester is obtained; 2, penicillin sulfoxide ester is adopted as a raw material, open loop rearrangement occurs in a solvent, and a thiazoline-aza-ketone derivative with double bonds at the tail end is obtained; 3 the thiazoline-aza-ketone derivative with double bonds at the tail end is adopted as a raw material, oxidizing is carried out, and thiazoline enol ester is obtained. The method is easy to operate, low in cost, good in product quality, high in yield and suitable for industrial production, and the total yield reaches 82%.

Description

technical field [0001] The invention belongs to the field of compound preparation methods, in particular to a preparation method of thiazoline enol ester. Background technique [0002] Cephalosporin 7-amino-3-chloro-3-cephalosporin-4-carboxylic acid is the key mother nucleus for the preparation of antibiotic cefaclor, and thiazoline enol ester is the key nucleus for the preparation of cephalosporin 7-amino-3-chloro-3 - The key intermediate of cephalosporin-4-carboxylic acid, and also the key intermediate for preparing a new generation of cephalosporins. In the process routes described in patents with application publication numbers CN102220403B, CN103387584A, and CN103694257A, the starting material used is thiazoline enol ester, or the synthesis of the starting material is thiazoline enol ester. So far, the synthetic route of thiazoline enol ester has only been announced by Shionogi Company, but ozone is used in the process, and it needs to be reacted at ultra-low temperatu...

Claims

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Application Information

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IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 王文秀吴金跃
Owner 浙江沙星科技股份有限公司
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