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Synthetic method for p-methyl phenyl serine ethyl ester

A technology of thiamphenylphenylserine ethyl ester and thiamphenylphenylserine copper, which is applied in the field of synthesis of florfenicol intermediates, can solve the problems of unfavorable environmental protection, disadvantages, and a large amount of waste acid, so as to protect the environment and improve Esterification conversion rate and the effect of reducing the amount of waste acid

Active Publication Date: 2017-06-30
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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Problems solved by technology

The above method (1), method (2) and method (3) all use a large amount of sulfuric acid to catalyze the esterification reaction, which will produce a large amount of waste acid in the production process, which is not conducive to environmental protection; in addition, when ethanol and sulfuric acid are heated The reaction produces water, which is not conducive to the forward progress of esterification

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  • Synthetic method for p-methyl phenyl serine ethyl ester

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preparation example Construction

[0022] The present invention relates to a kind of synthetic method of ethyl sulfonyl phenyl serine, comprising the following steps:

[0023] Reaction 1 (new), add diethyl sulfate, ethanol (1eq), sulfuric acid (1eq) and p-thymphenylphenylserine copper salt (1eq) into the reaction kettle, and react under reflux for 5-9 hours, and monitor the esterification by HPLC When the conversion rate is greater than 95% to 99%, the reaction ends. Insulated pressure filtration, the filter cake is washed with a small amount of ethanol, and the filter cake is copper sulfate (recovered for later use). Cool the mother liquor to crystallize, drop to -5~0°C for suction filtration, recover the mother liquor for further use; the filter cake is p-thiamphenylphenylserine ethyl sulfate, and then dissolve in water, remove copper with sodium sulfide, and obtain p-methylsulfone through ammonia ammonia analysis phenylserine ethyl ester.

[0024] Reaction 2 (applied mechanically), add recovered mother liq...

Embodiment 1

[0032] 1) Add 200g of diethyl sulfate, 20g of ethanol, 34g of sulfuric acid and 100g of p-thymphenylphenylserine copper salt into a 1000mL reactor, stir at room temperature for 1h, heat and reflux for 5-9h, and monitor the conversion rate of esterification by HPLC. 95% to 99% of the reaction is over. Insulated pressure filtration, the filter cake was washed with a small amount of 30g of hot ethanol, and the filter cake was copper sulfate (recovered for later use). Cool the mother liquor to crystallize, drop to -5 ~ 0 ℃ for suction filtration, and recover the mother liquor for use; Add ammonia water dropwise at 5°C to adjust the pH to 8.0; filter with suction and dry to obtain 93 g (about 94%) of p-thymphenylphenylserine ethyl ester as a white solid.

[0033] 2) Add 300g of recovered mother liquor, 24g of ethanol, 35g of sulfuric acid and 100g of p-thymphenylphenylserine copper salt into the reaction kettle, stir at room temperature for 1h, heat and reflux for 5-9h, and monito...

Embodiment 2

[0035] 1) Add 250g of diethyl sulfate, 24g of ethanol, 45g of sulfuric acid and 100g of p-thymphenylphenylserine copper salt into a 1000mL reactor, stir at room temperature for 1h, heat and reflux for 5-9h, and monitor the conversion rate of esterification by HPLC. 95% to 99% of the reaction is over. Insulated pressure filtration, the filter cake was washed with a small amount of 30g of hot ethanol, and the filter cake was copper sulfate (recovered for later use). Cool the mother liquor to crystallize, drop to -5 ~ 0 ℃ for suction filtration, and recover the mother liquor for use; Add ammonia water dropwise at 5°C to adjust the pH to 8.0; filter with suction and dry to obtain 91 g (about 92%) of p-thymphenylphenylserine ethyl ester as a white solid.

[0036] 2) Add 300g of recovered mother liquor, 27g of ethanol, 48g of sulfuric acid and 100g of p-thymphenylphenylserine copper salt into the reaction kettle, stir at room temperature for 1h, heat and reflux for 5~9h, and monito...

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Abstract

The invention provides a synthetic method for p-methyl phenyl serine ethyl ester. The method comprises the following steps: adding diethyl sulfate, ethanol, sulfuric acid and p-diphenylserine copper salt in a reaction vessel, performing a backflow reaction, monitoring the esterification conversion rate at 95-99% and completing the reaction; cooling the mother liquor after insulation and press filtration and crystallizing the material, performing pumping filtration after cooling to -5-0 DEG C, dissolving an obtained filter cake with water and removing copper by sodium sulfide, performing ammoniacal liquor analysis to obtain the product. The method has the advantages that average yield can reach 95%, product purity can reach more than 98%, waste water is little, and the method is environmentally friendly.

Description

technical field [0001] The invention relates to a method for synthesizing a florfenicol intermediate, in particular to a method for synthesizing p-thymphenylphenylserine ethyl ester with high yield, less waste water and environmental protection. 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. It is a kind of broad-spectrum antibacterial drug, which was first listed in Japan in 1990. In 1993, Norway approved the drug to treat salmon furunculosis. In 1995, France, the United Kingdom, Austria, Mexico and Spain approved it to treat bovine respiratory bacterial diseases. In Japan and Mexico, it is also approved as a feed additive for pigs to prevent and treat bacterial diseases in pigs. my country has already passed the approval of this drug. Among them, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/48
CPCC07C315/04C07C317/48
Inventor 余志强冯启峰高鹏徐剑锋曾淼
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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