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Technique for producing D-(-)-p-hydroxyphenylglycine by aqueous-phase resolution method

A technology of p-hydroxyphenylglycine and water phase is applied in the technical field of producing D-(-)-p-hydroxyphenylglycine by an aqueous phase splitting method, and can solve the problems of high cost, large degree of operation, resource limitation and the like

Inactive Publication Date: 2009-12-30
HENAN NEWLAND PHARMA
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

And achieved pilot test results, but this method is to use acetone with low boiling point as solvent, and the operation degree is large during industrialization, and the cost is high
[0014] D-HPG with optical purity can be obtained by splitting with chiral resolving agents such as dextrotartaric acid and 8-bromocamphorsulfonic acid, but it is difficult to realize industrialization due to expensive resolving agents and limited resources

Method used

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  • Technique for producing D-(-)-p-hydroxyphenylglycine by aqueous-phase resolution method
  • Technique for producing D-(-)-p-hydroxyphenylglycine by aqueous-phase resolution method
  • Technique for producing D-(-)-p-hydroxyphenylglycine by aqueous-phase resolution method

Examples

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Effect test

example 1

[0031] In a 5000L enamel kettle, put 1600Kg of deionized water, 800Kg of DL-HPG, PTS.H 2 O950Kg was heated up to dissolve, and the temperature of the solution was lowered to 20°C and dried by centrifugation. Get 1520KgDL-HPG·PTS salt

example 2

[0033] Put 1400Kg of deionized water into a 5000L enamel kettle. DL-HPG·PTS470Kg, D-HPG·PTS471Kg, heat until completely dissolved, cool down to 50°C, measure the optical rotation of the solution α=-3°, continue to cool down to 30°C and appear Crystallization, continuously check the optical rotation of the mother liquor, and centrifuge when α=2.5~3. Get D-HPG·PTS200Kg, [α] 20 D =-60°, optical purity 90%, mother liquor optical rotation α=+3°

example 3

[0035] Put the above mother liquor of α=+3° into a dextrorotational separation kettle, 200KgD-HPG·PTS, heat and dissolve and cool down to 50°C to measure the solution α=+3°, continue to cool down to about 30°C to appear crystallization, and constantly check the optical rotation of the mother liquor. When α=-2.5~-3, centrifuge to obtain L-HPG·PTS205Kg, [α] 20 D =+60°, optical purity 90%, mother liquor optical rotation α=-3.1°

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Abstract

The invention provides a technique for producing D-(-)-p-hydroxyphenylglycine by aqueous-phase resolution method, which belongs to the field of pharmaceutical intermediate production. With the wide application of amoxicillin, cefadroxil and the like, the market of a side chain D-HPG thereof continually expands, and people pay more and more attention to synthesis and resolution methods thereof. By chemical methods, the technique uses resolution agent and racemic DL-HPG to form salts and utilizes different solubility thereof in particular solvents to separate two optical isomers so as to achieve the aim of resolution. The technique for producing D-(-)-p-hydroxyphenylglycine by aqueous-phase resolution method uses non-chiral resolution agents which are cheap and readily available and selects water as a solvent, thereby obtaining the D-HPG with low cost and high optical purity.

Description

technical field [0001] The present invention relates to the production method of the compound with following structure: [0002] [0003] Its chemical name is D-(-)-p-hydroxyphenylglycine (D-HPG for short). This compound is the side chain of semi-synthetic β-lactam antibiotics. It can be combined with 6-APA(II) to synthesize amoxicillin [0004] [0005] Combining with 7-ADCA(III) can synthesize amoxil cephalosporin, [0006] [0007] Wherein: X=H, it can also be used to synthesize broad-spectrum antibiotics such as cefprozil and cefoperazone. Background technique [0008] With the massive application of amoxicillin, amoxil cephalosporin, etc., the side chain D-HPG market continues to expand, and its synthesis and resolution methods are increasingly attracting people's attention. [0009] There is a chiral center in compound I, and all the racemates produced by chemical synthesis, that is, DL-(±)HPG, must be resolved to obtain the required D-(-)-HPG. [0010] The...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/34C07B57/00
Inventor 谢建中
Owner HENAN NEWLAND PHARMA
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