D-p-hydroxyphenyl glycine preparation process

A technology for L-para-hydroxyphenylglycine and para-hydroxyphenylglycine, which is applied in the field of organic compound synthesis, can solve the problems of waste water treatment requiring large energy consumption, unfavorable environmental protection, increased process loss and the like, and achieves a guaranteed first pass rate and production cycle The effect of shortening, energy and labor reduction

Active Publication Date: 2019-11-19
HENAN NEWLAND PHARMA
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0004] The characteristics of the above three synthetic methods of L-p-hydroxyphenylglycine are that the synthesis route is longer and the production cycle is longer. Their commonality is that solid-state mixed-rotation p-hydroxyphenylglycine should be made first, and then the solid-state mixed-rotation p-hydroxyphenylglycine should be prepared. Add acid to dissolve glycine into an aqueous solution, and then split it. There are many steps in the intermediate process, and the increase in process loss leads to relatively high production costs; Washing with water or organic solvents will produce a large amount of waste water, which is not only a waste of water resources, but also requires a lot of energy to treat waste water, which is not conducive to environmental protection

Method used

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Examples

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Embodiment 1

[0037]In a 1000ml reaction flask, put 1 mol of phenol, 1 mol of 20% glyoxylic acid, and 1.2 mol of sulfamic acid, then add 0.2 g of composite catalyst, then heat up to synthesize p-hydroxyphenylglycine-sulfate, and monitor the HPG content by HPLC to reach 99.2%; Next, add 25g of pure water-methanol mixture to the obtained reaction solution, add 0.5g of powdered activated carbon and decolorize and remove impurities at 60-65°C for 30min to obtain pure hydroxyphenylglycine sulfate Reaction solution; then add 165g of 40% phenylethylsulfonic acid solution, make it react at 80°C for 2.5h, obtain L-p-hydroxyphenylglycine-phenylethylsulfonic acid suspension; obtain solid L-p-hydroxyphenylglycine-phenylethylsulfonic acid after centrifugation The double salt of sulfonic acid, then, make it hydrolyze with 25% sodium hydroxide solution, control the pH value to 5.5, and precipitate the crystals of L-p-hydroxyphenylglycine, and then obtain the L-p-hydroxyphenylglycine crystal through crystal...

Embodiment 2

[0039] In a 1000ml reaction flask, put 1 mol of phenol, 1 mol of 20% glyoxylic acid, and 1.2 mol of sulfamic acid, then add 0.2 g of composite catalyst, then heat up to synthesize p-hydroxyphenylglycine-sulfate, and monitor the HPG content by HPLC to reach 99.0%; Next, add 25g of pure water-ethanol mixture to the obtained reaction solution, add 0.5g of powdered activated carbon and decolorize and remove impurities for 30min at 60-65°C to obtain pure hydroxyphenylglycine sulfate Reaction solution; then add 165g of 40% phenylethylsulfonic acid solution, make it react at 80°C for 2.5h, obtain L-p-hydroxyphenylglycine-phenylethylsulfonic acid suspension; obtain solid L-p-hydroxyphenylglycine-phenylethylsulfonic acid after centrifugation The double salt of sulfonic acid, next, make it hydrolyze with 20% ammonia water, control the pH value to 5.3, and then obtain crystals of L-p-hydroxyphenylglycine through crystal growth and solid-liquid separation, and the filtrate is desalted and ...

Embodiment 3

[0041] In a 1000ml reaction flask, put 1 mol of phenol, 1 mol of 20% glyoxylic acid, and 1.2 mol of sulfamic acid, then add 0.15 g of composite catalyst, and then heat up to synthesize p-hydroxyphenylglycine-sulphate. HPLC monitors that the HPG content reaches 99.3%; Next, add 18g of pure water-methanol mixture to the obtained reaction solution, add 01g of powdered activated carbon, and decolorize and remove impurities for 30min at 60-65°C to obtain pure vortex p-hydroxyphenylglycine sulfate reaction solution; then add 165g of 40% phenylethylsulfonic acid solution and make it react at 75°C for 2.5h to obtain a suspension of L-p-hydroxyphenylglycine-phenylethylsulfonic acid; centrifuge to obtain solid L-p-hydroxyphenylglycine-phenylethylsulfonate The double salt of acid, then, make it hydrolyze with 20% ammonia water, control the pH value to 5.6, and then obtain crystals of L-p-hydroxyphenylglycine through crystal growth and solid-liquid separation, and the filtrate is desalted ...

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Abstract

The present invention relates to the field of compound synthesis, and discloses a D-p-hydroxyphenyl glycine (short for DHPG) preparation process, which comprises: synthesizing a DL-para-hydroxyphenylglycine sulfate solution (DL-para-hydroxyphenyl glycine is short for HPG) by using phenol, glyoxylic acid and the like as raw materials; purifying, adding a resolving agent, and performing an asymmetric resolution reaction to obtain a D-p-hydroxyphenyl glycine-phenylethane sulfonic acid double salt; adding an alkali liquid to the obtained double salt in a dropwise manner, and carrying out a hydrolysis reaction and other operations to obtain a D-p-hydroxyphenyl glycine crystal; and carrying out further treatment on the mother liquor containing the resolving agent phenylethane sulfonic acid, andrecycling. According to the present invention, the preparation process is mainly characterized in that the composite catalyst is introduced, and the three steps are eliminated, such that the production cycle is shortened by 12 h; the short synthesis route is short, and the loss is low, such that the yield of D-p-hydroxyphenyl glycine is increased by 7-9%, and the water consumption is reduced by 15-16%; the technical prejudice of the previous D-p-hydroxyphenyl glycine preparation process in the prior art is objectively overcome, and the unexpected effect is achieved; and the D-p-hydroxyphenylglycine preparation process has characteristics of production cost reducing and production efficiency improving, and easily achieves water resource saving and environment protection.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a preparation process of L-p-hydroxyphenylglycine. Background technique [0002] D-p-hydroxyphenylglycine (D-p-hydroxyphenylglycine), referred to as DHPG, molecular weight 167.16, appearance is white crystalline powder, slightly soluble in ethanol and water, easily soluble in acid or alkali to form salt, melting point is 225 ℃ ~ 227 ℃, content >98.5%, the specific optical rotation is -155~-161°; L-p-hydroxyphenylglycine is not only an important fine chemical product and important pharmaceutical intermediate, but also a broad-spectrum antibiotic such as amoxicillin, cefadroxil and cefoperazone It is an indispensable side chain acid in the synthesis of ketones, cefuroxime and cefadroxol. [0003] The industrial synthesis method of L-p-hydroxyphenylglycine mainly contains following several at present: 1 is raw material with glyoxylic acid, phenol, sulfamic a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/08C07C227/34C07C227/18C07C229/36C07C303/22C07C309/24
CPCC07C227/08C07C227/34C07C227/18C07C303/22C07B2200/13C07C229/36C07C309/24
Inventor 谢建中刘超师红亮
Owner HENAN NEWLAND PHARMA
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