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Recovering technology of methyl (E/Z)-2-(2-aminothiazole-4-yl)-2-pentenoate waste liquid

A technology of methyl pentenoate and aminothiazole, applied in the direction of organic chemistry, can solve problems such as high cost, increased cost pressure, and environmental pollution, and achieve the effects of good quality, reduced production cost, and simple reaction process

Active Publication Date: 2017-05-31
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, the synthesis of cefcapene pivoxil all uses the derivative docking process of (Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid and 7-ACA, wherein, (Z )-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid is one of the key factors affecting its quality and yield, (Z)-2-(2-aminothiazole-4 -yl)-2-pentenoic acid methyl ester is an intermediate in the synthesis of (Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid, due to thermodynamics or kinetics In the process of synthesizing (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester, the by-product (E)-2-(2-aminothiazol-4-yl )-2-pentenoic acid methyl ester accounts for about 45%, and a small amount of (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl The ester enters the mother liquor, thereby producing (E / Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester waste liquid, which not only reduces the production of (Z)-2- The yield of (2-aminothiazol-4-yl)-2-pentenoic acid methyl ester, and environmental protection treatment difficulty is big, cost is high, pollutes environment
[0003] There is no reference to (E)-2-(2-aminothiazol-4-yl) -2-Pentenoic acid methyl ester is generally treated as an impurity, which not only causes waste of raw materials, but also increases the cost pressure of enterprises

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 900 mL of water to 300 g of (E / Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester waste solution (E:Z=95:5), and then place it in volume In a 5L photochemical reactor, 220nm ultraviolet light generated by a 500W hydrogen lamp was used to irradiate for 2 hours under stirring. The temperature in the reactor was controlled at 30°C. After the reaction, the reaction solution obtained was detected by HPLC: E / Z= 35:65, 350g of 6N hydrochloric acid crystallization was added dropwise to the reaction solution, incubated for 1h, and suction filtered to obtain 180g of (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester, the product Yield 60%, purity 99.72%.

Embodiment 2

[0025] Add 900 mL of water to 300 g of (E / Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester waste solution (E:Z=95:5), and then place it in volume In a 5L photochemical reactor, 287nm ultraviolet light generated by a 500W deuterium lamp was used to irradiate for 1.5h under stirring, and the temperature in the reactor was controlled at 35°C. After the reaction, the reaction solution obtained was detected by HPLC: E:Z =25:75, 415g of 6N hydrochloric acid crystallization was added dropwise to the reaction solution, incubated for 0.8h, and suction filtered to obtain 205g of (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester , the product yield is 68.3%, and the purity is 99.85%.

Embodiment 3

[0027] Add 600mL of methanol to 300g of (E / Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester waste solution (E:Z=95:5), then place it in capacity In a 2L photochemical reactor, the 220nm ultraviolet light produced by a 500W hydrogen lamp was used to irradiate for 5h under stirring, and the temperature in the reactor was controlled at 27°C. The reaction solution obtained after the reaction was detected by HPLC: E:Z= 40:60, 290g of 6N hydrochloric acid crystallization was added dropwise to the reaction solution, incubated for 1.5h, and suction filtered to obtain 165g of (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester, The product yield is 55%, and the purity is 99.82%.

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Abstract

The invention relates to a recovering technology of a methyl (E / Z)-2-(2-aminothiazole-4-yl)-2-pentenoate waste liquid, and belongs to the technical field of the preparation of medicine intermediates. The recovering technology comprises the following steps: mixing the methyl (E / Z)-2-(2-aminothiazole-4-yl)-2-pentenoate waste liquid with a solvent, adding the obtained solution to a photochemical reactor, carrying out a reaction, dropwise adding 6 N of hydrochloric acid, crystallizing the obtained solution, and carrying out heat insulation and suction filtration to obtain methyl (Z)-2-(2-aminothiazole-4-yl)-2-pentenoate. The recovering technology directly converting methyl (E)-2-(2-aminothiazole-4-yl)-2-pentenoate into the methyl (Z)-2-(2-aminothiazole-4-yl)-2-pentenoate has the advantages of the environmental protection problem brought by waste residues, simple reaction process, no consumption of other reaction raw materials in the process, and reduction of the production cost.

Description

technical field [0001] The invention relates to a recovery and treatment process of (E / Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester waste liquid, belonging to the technical field of preparation of pharmaceutical intermediates. Background technique [0002] At present, the synthesis of cefcapene pivoxil all uses the derivative docking process of (Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid and 7-ACA, wherein, (Z )-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid is one of the key factors affecting its quality and yield, (Z)-2-(2-aminothiazole-4 -yl)-2-pentenoic acid methyl ester is an intermediate in the synthesis of (Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid, due to thermodynamics or kinetics In the process of synthesizing (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester, the by-product (E)-2-(2-aminothiazol-4-yl )-2-pentenoic acid methyl ester accounts for about 45%, and a small amount of (Z)-2-(2-ami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 郑庚修孙智源杨兆钰李勇
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD