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DL-p-methylsulfonylphenyl serine ethyl ester preparation method

A methylsulfonyl phenylserine ethyl ester, p-methylsulfonyl technology, applied in the field of preparation of DL-p-methylsulfonyl phenylserine ethyl ester, can solve the problems of low product yield, high cost, strong corrosiveness and the like, and achieves The effect of protecting the environment, avoiding danger and improving operational efficiency

Inactive Publication Date: 2020-02-11
JIANGSU YUXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] There are more or less defects in the various existing 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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  • DL-p-methylsulfonylphenyl serine ethyl ester preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1) Add 83.7g (0.6mol) ethyl glycine hydrochloride into 500mL ethanol, heat to reflux, and dissolve ethyl glycine hydrochloride in ethanol;

[0022] 2) 66.3 (0.3mol) basic copper carbonate (Cu 2 (OH) 2 CO 3 ) was dissolved in 100mL ammonia water, and then added into the solution obtained in step 1);

[0023] 3) Add KOH to adjust the pH of the solution to 10.5 to 10.6 in step 2), add 92g (0.5mol) p-thiamphenicol benzaldehyde to react, keep the temperature at 78 to 85°C during the reaction, and control the pH to 10.0 to 11.0; by HPLC Monitor the progress of the reaction; when the percentage of p-thiamphenicol benzaldehyde calculated by the area normalization method<1%, the reaction ends.

[0024] 4) After the reaction is over, recover the ethanol in the reacted substance, then add ammonia water to the residue, adjust the pH to 8.0-8.2, cool the solution to 0-5°C, filter, wash with ice water, and dry to obtain 140.8g (0.49mol) p-thymphenylphenylserine ethyl ester, yield...

Embodiment 2

[0028] 1) Add 90.6g (0.65mol) ethyl glycine hydrochloride into 500mL ethanol, heat to reflux, and dissolve ethyl glycine hydrochloride in ethanol;

[0029] 2) 77.4 (0.35mol) basic copper carbonate (Cu 2 (OH) 2 CO 3 ) was dissolved in 100mL ammonia water, and then added into the solution obtained in step 1);

[0030] 3) In step 2), add KOH to adjust the pH of the solution=10.5~10.6, add 92g (0.5mol) p-thiamphenicol benzaldehyde for reaction, keep warm at 78~82°C during the reaction, control pH=10.0~11.0; by HPLC Monitor the progress of the reaction; when the percentage of p-thiamphenicol benzaldehyde calculated by the area normalization method<1%, the reaction ends.

[0031] 4) After the reaction is over, recover the ethanol in the reacted substance, then add ammonia water to the residue, adjust the pH=8.0-8.2, cool the solution to 0-5°C, filter, wash with ice water, and dry to obtain 141.4g (0.492mol) p-thymphenylphenylserine ethyl ester, yield: 98.4%, product purity 99.3%...

Embodiment 3

[0034] 1) Add 97.6g (0.7mol) ethyl glycine hydrochloride into 500mL ethanol, heat to reflux, and dissolve ethyl glycine hydrochloride in ethanol;

[0035] 2) 71.9 (0.325mol) basic copper carbonate (Cu2(OH)2CO3) was dissolved in 100mL ammonia water, and then added to the solution obtained in step 1);

[0036] 3) In step 2), add KOH to adjust the pH of the solution=10.5~10.6, add 92g (0.5mol) p-thiamphenicol benzaldehyde for reaction, keep warm at 78~82°C during the reaction, control pH=10.0~11.0; by HPLC Monitor the progress of the reaction; when the percentage of p-thiamphenicol benzaldehyde calculated by the area normalization method<1%, the reaction ends.

[0037] 4) After the reaction is over, recover the ethanol in the reacted substance, then add ammonia water to the residue, adjust the pH=8.0-8.2, cool the solution to 0-5°C, filter, wash with ice water, and dry to obtain 141.7g (0.493mol) p-thymphenylphenylserine ethyl ester, yield: 98.6%, product purity 99.4%.

[0038]...

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Abstract

The invention discloses a DL-p-methylsulfonylphenyl serine ethyl ester preparation method, which comprises: 1) adding glycine ethyl ester hydrochloride into ethanol, and carrying out heating reflux; 2) dissolving basic cupric carbonate in ammonia water, and adding into the solution obtained in the step 1); 3) adding KOH into the solution obtained in the step 2) to adjust the pH value of the solution, and adding p-methylsulphonyl benzaldehyde, carrying out a reaction; and 4) after the reaction is finished, recovering ethanol in the reacted substance, adding ammonia water into the residue, regulating the pH value, cooling the solution, filtering, washing with ice water, and drying to obtain the p-methylsulfonylphenyl serine ethyl ester. According to the invention, the target product is generated by carrying out a one-step reaction on glycine ethyl ester hydrochloride and p-methylsulphonyl benzaldehyde under the catalysis of basic cupric carbonate and an alkali, wherein the reaction process does not require the use of concentrated sulfuric acid so as to completely avoid the generation of strong acid wastewater, protect and the environment, avoid the possible danger in the sulfuric acid transportation and production process, achieve the safety and easily improve the operation efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular 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: C 12 h 17 NO 5 S, slightly soluble in water, soluble in organic solvents. DL-p-thiamphenicol phenylserine ethyl ester is an important intermediate for the synthesis of drugs such as broad-spectrum antibiotics thiamphenicol and florfenicol, and its 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 act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/48B01J27/236
CPCB01J27/236C07C315/04C07C317/48
Inventor 程红伟黄剑张治国程云涛
Owner JIANGSU YUXIANG CHEM
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