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Preparation method of DL-p-methylsulfonylphenyl serine ethyl ester

The technology of methylsulfonyl phenylserine ethyl ester and methylsulfonyl phenylserine copper is applied in the field of preparation of DL-p-methylsulfonyl phenylserine ethyl ester, and can solve the problems of strong corrosiveness, high cost, low product yield and the like

Inactive Publication Date: 2012-05-09
JIANGSU YUXIANG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process yield is high, but the use of ethanol is too large, resulting in high product costs
[0010] In summary, there are various defects in the existing various synthetic methods, or the product yield is low, or the corrosion is too strong in the reaction process, or the cost is too high
Existing technical routes need to be improved in terms of environmental friendliness and cost

Method used

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  • Preparation method of DL-p-methylsulfonylphenyl serine ethyl ester
  • Preparation method of DL-p-methylsulfonylphenyl serine ethyl ester
  • Preparation method of DL-p-methylsulfonylphenyl serine ethyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Esterification: Add 120 g of absolute ethanol and 35 g of benzene in a four-necked flask equipped with mechanical stirring, reflux condenser and thermometer, slowly add 60 g of concentrated sulfuric acid dropwise at room temperature, and add 58 g of p-thiamphenicol after the addition is completed. Phenylserine copper salt, warm to reflux. During the reflux reaction process, the moisture generated by the reaction was continuously removed through the water separator, and the reflux reaction was performed for 30 hours. After the reaction was completed, the temperature was slightly lowered while hot and the filter cake was copper sulfate. The filtrate was placed at 0°C overnight for crystallization, and finally filtered by suction to obtain DL-p-thymphenylphenylserine ethyl sulfate.

[0026] (2) Dissociation and neutralization: Add 75g of deionized water into a four-neck flask equipped with stirring, reflux condenser and thermometer, and add the above-mentioned DL-p-thy...

Embodiment 2

[0028] (1) Esterification: Add 120 g of absolute ethanol and 70 g of toluene to a four-necked flask equipped with mechanical stirring, reflux condenser and thermometer, slowly add 60 g of concentrated sulfuric acid dropwise at room temperature, and add 58 g of p-thiamphenicol after the addition is completed. Phenylserine copper salt, warm to reflux. During the reflux reaction process, the moisture generated by the reaction was continuously removed through the water separator, and the reflux reaction was carried out for 18 hours. After the reaction was completed, the temperature was slightly lowered while hot and the filter cake was copper sulfate. The filtrate was placed at 0°C overnight for crystallization, and finally filtered by suction to obtain DL-p-thymphenylphenylserine ethyl sulfate.

[0029] (2) Dissociation and neutralization: Add 75g of deionized water into a four-neck flask equipped with stirring, reflux condenser and thermometer, and add the above-mentioned DL-p-t...

Embodiment 3

[0031] (1) Esterification: Add 120 g of absolute ethanol and 46.4 g of xylene in a four-necked flask equipped with mechanical stirring, reflux condenser and thermometer, slowly add 60 g of concentrated sulfuric acid dropwise at room temperature, and add 58 g of p-toluene after the dropwise addition Sulfonylphenylserine copper salt, heated to reflux. During the reflux reaction process, the moisture generated by the reaction was continuously removed through the water separator, and the reflux reaction was performed for 20 hours. After the reaction was completed, the temperature was slightly lowered while hot and the filter cake was copper sulfate. The filtrate was placed at 0°C overnight for crystallization, and finally filtered by suction to obtain DL-p-thymphenylphenylserine ethyl sulfate.

[0032] (2) Dissociation and neutralization: Add 75g of deionized water into a four-neck flask equipped with stirring, reflux condenser and thermometer, and add the above-mentioned DL-p-thy...

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Abstract

The invention provides a preparation method of DL-p-methylsulfonylphenyl serine ethyl ester. A main initial raw material of p-methylsulfonylphenylserine copper salt is successively treated with esterification, dissociation and neutralization to prepare the DL-p-methylsulfonylphenyl serine ethyl ester. Benzene, toluene, xylene, hexane and cyclohexane are used as water carrying agents in the esterification reaction to promote progressing of the esterification reaction. The synthetic method of the invention has mild reaction conditions, simple technical operations and a total yield higher than 90%.

Description

technical field [0001] The invention relates to a preparation method of DL-p-thymphenylphenylserine ethyl ester. Background technique [0002] DL-p-thymphenylphenylserine ethyl ester, white to off-white crystal, molecular formula: C12H17NO5S, slightly soluble in water, soluble in organic solvents. DL-p-thiamphenicol phenylserine ethyl ester is an important intermediate for the synthesis of broad-spectrum antibiotics such as thiamphenicol and florfenicol. The molecular structure is as follows: [0003] [0004] Thiamphenicol, English / Latin name: Thiamphenicol, alias thiamphenicol, thiamphenicol chloramphenicol. It is white crystalline powder; odorless. It is used for respiratory, urinary tract, and intestinal infections caused by sensitive bacteria such as Haemophilus influenzae, Escherichia coli, and Salmonella. It is an analogue of chloramphenicol with a similar antibacterial activity and range to chloramphenicol. At present, most of the domestic production adopts th...

Claims

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Application Information

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IPC IPC(8): C07C317/48C07C315/04
Inventor 张治国程云涛
Owner JIANGSU YUXIANG CHEM
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