P-Methyl sulfone phenyl ethyl serinate and synthetic method thereof

A technology of thiamphenylphenylserine ethyl ester and glycine ethyl ester hydrochloride, which is applied in the synthesis of p-thymphenylphenylserine ethyl ester and p-thymphenylphenylserine ethyl ester field, which can solve unfavorable esterification Forward progress, unfavorable production rate, unfavorable environmental protection and other issues, to achieve the effect of improving reaction efficiency, beneficial to environmental protection, and simplifying operations

Active Publication Date: 2018-08-07
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0008] The above three methods all use a large amount of sulfuric acid for catalytic esterification, and a large amount of waste acid is produced during production, which is not conducive to environmental protection; , all need to be very cautious, so as not to cause harm to personnel and equipment, which is not conducive to increasing production rate
[0009] In addition, the above-mentioned method often needs to use p-thiamphenicyl benzaldehyde as the startin

Method used

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  • P-Methyl sulfone phenyl ethyl serinate and synthetic method thereof
  • P-Methyl sulfone phenyl ethyl serinate and synthetic method thereof
  • P-Methyl sulfone phenyl ethyl serinate and synthetic method thereof

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Example Embodiment

[0036] The present invention discloses a synthetic method of p-methylsulfonyl phenyl serine ethyl ester, which comprises the following steps:

[0037] S1. Add the set dose of ethyl glycinate hydrochloride and methanol into the reaction kettle, and raise the temperature to between 30-80°C, preferably between 40-65°C. When the temperature rises, combine with stirring to make ethyl glycinate hydrochloride Dissolve in methanol to form the first solution.

[0038] S2. Add a set dose of copper sulfate pentahydrate to the first solution to dissolve it, keep it at 30-80°C, preferably at 40-65°C, and stir for 0.5h to form a second solution. The reaction produces ethyl glycinate copper complex.

[0039] S3, adding an organic base to the second solution, the organic base is preferably one of triethylamine, dimethylamine, and ethylenediamine, so that the pH value of the second solution is adjusted to alkaline reaction conditions, namely: Make the pH of the second solution between 7.0 and 10.0,...

Example Embodiment

[0045] Example 1

[0046] Add 500g (15.6mol) of methanol and 73.9g (0.53mol) of ethyl glycinate hydrochloride into a 1000ml reaction flask, stir and heat to 50-55℃, so that ethyl glycinate hydrochloride is completely dissolved in methanol to form the first Solution.

[0047] Then, 67.5 g (0.27 mol) of copper sulfate pentahydrate was added to the first solution, stirred to completely dissolve, and kept at 50-55° C. and stirred for 0.5 h to obtain the second solution.

[0048] Then, start to add triethylamine dropwise to the second solution to adjust the pH value of the second solution to 8.5-9.0, then add 92g (0.5mol) of p-methylsulfonyl benzaldehyde, and keep the reaction at 50-55℃ for 30h During the incubation period, the pH value is controlled between 8.5-9.0. During the reaction, the progress of the reaction is monitored by HPLC. When the percentage of p-methylsulfonyl benzaldehyde calculated by the area normalization method is less than 2%, the reaction is deemed to be complete ...

Example Embodiment

[0050] Example 2

[0051] Add 500 g (15.6 mol) of methanol and 76.7 g (0.550 mol) of ethyl glycine hydrochloride into a 1000 ml reaction flask, stir and raise the temperature to 40-45° C. to completely dissolve ethyl glycine hydrochloride to form the first solution.

[0052] Then 71.2 g (0.285 mol) of copper sulfate pentahydrate was added to the first solution, stirred to make it completely dissolved, and kept at 40-45° C. and stirred for 0.5 h to obtain the second solution.

[0053] Then start to add dimethylamine methanol solution dropwise to the second solution to adjust the PH value of the second solution to between 9.0-9.3, and then add 92g (0.5mol) of p-methylsulfonyl benzaldehyde and keep it at 40-45℃ Incubate the reaction for 30 hours, and control the pH between 9.0-9.3 during the incubation reaction. During the reaction, monitor the progress of the reaction by HPLC. When the percentage of p-methylsulfonyl benzaldehyde calculated by the area normalization method is less than ...

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Abstract

The invention discloses a synthetic method of P-methyl sulfone phenyl ethyl serinate, comprising the steps of S1, adding ethyl glycinate hydrochloride into methanol, and heating to dissolve to form afirst solution; S2, adding copper sulfate pentahydrate in the first solution to form a second solution by dissolving; S3, adjusting PH value of the second solution to meet the condition for alkaline reaction, adding P-methylsufonyl benzaldehyde to allow reaction, and holding the temperature and controlling the PH value to keep reaction condition values during reaction; S4, recycling methanol in the reacted materials, adding water to the residue to form a third solution, cooling, and centrifugally separating to obtain P-methyl sulfone phenyl ethyl serinate. The ethyl glycinate hydrochloride andP-methylsufonyl benzaldehyde are subjected to further reaction under the catalytic action of copper sulfate and an organic base to generate a target product; no sulfuric acid is used in the reactionprocess, the amount of waste acid in waste water is decreased, and the environment is protected; dangers that may occur during sulfuric acid transport and production are avoided, better safety is provided, and operating efficiency can be improved.

Description

technical field [0001] The invention relates to a florfenicol intermediate and a synthesis method thereof, in particular to a synthesis method of p-thiamphenylphenylserine ethyl ester with high yield, less waste water and environmental protection and p-thiamphenylphenylserine ethyl ester ester. Background technique [0002] Florfenicol, also known as fluprofen and fluthiamphenicol, is a white or off-white crystalline powder, odorless, and bitter in taste. It is a new type of chloramphenicol for veterinary medicine that was successfully developed in the late 1980s. A class of broad-spectrum antibacterial drugs, which produce broad-spectrum antibacterial effects by inhibiting the activity of peptidyltransferases, and have a broad antibacterial spectrum, including various Gram-positive and negative bacteria and mycoplasma. [0003] It was first launched in Japan in 1990. In 1993, Norway approved the drug to treat salmon furunculosis. In 1995, France, the United Kingdom, Austri...

Claims

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Application Information

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IPC IPC(8): C07C315/04C07C317/48
Inventor 余志强徐剑锋曾淼朱家可卫海浩沈洁
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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