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Preparation method of para-hydroxybenzol gylcine

A technology of p-hydroxyphenylglycine and nitro group is applied in the field of preparation of D-p-hydroxyphenylglycine, which can solve problems such as low yield and long reaction time, and achieve the effects of reducing side reactions, low price and lowering production cost.

Inactive Publication Date: 2007-10-03
BAOSHAN IRON & STEEL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction time of this method is as long as 22 hours, and there are defects such as long reaction time and low yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In 80ml glacial acetic acid, add 8.5 grams (0.05mol) DL-p-hydroxyphenylglycine and 16.9 grams (0.05mol) (+)-3-bromo-8-ammonium camphorsulfonate, in N 2 Under the condition of protection and stirring, the temperature was raised to 70°C, and after the formation of a white suspension, 2.5g (0.025mol) of sulfuric acid was slowly added dropwise. After one hour, the temperature was slowly lowered to 10° C., and the formed double salt was fully analyzed. Filter under reduced pressure to obtain 24.58 grams of white crystalline D-p-hydroxyphenylglycine (+)-3-bromo-8-camphorsulfonic acid double salt, the yield is 97%, after washing with a small amount of acetic acid, place in vacuum drying Dry in box. Take 80 grams of filtrate, add it to a distillation bottle, raise the temperature of the oil bath, control the distillation temperature between 120 ° C and 140 ° C, collect the acetic acid fraction, and wait until the distillation ends when there is basically no distillate. A total...

Embodiment 2

[0025] In 50ml glacial acetic acid, add 10.5 grams of (+)-3-bromo-8-camphorsulfonic acid potassium salt and 5 grams of DL-p-hydroxyphenylglycine that 10.5 grams of embodiment 1 reclaims and mix, in N 2 Under the conditions of protection and stirring, the temperature was raised to 70°C, and 1.5g (0.015mol) of sulfuric acid was slowly added dropwise after forming a white suspension. After one hour, the temperature was slowly lowered to 10° C., and the formed double salt was fully analyzed. Filter under reduced pressure to obtain 14.3 grams of white crystalline D-p-hydroxyphenylglycine (+)-3-bromo-8-camphorsulfonic acid double salt, be dissolved in 35ml 50v / v% ethanol aqueous solution, then add 2.1 grams of carbonic acid Potassium, heat up to 50°C while stirring, after reacting for 2 hours, cool down to 20°C, filter under reduced pressure to obtain the filtrate and white precipitate, wash the white precipitate with a small amount of ethanol, and dry in vacuum to obtain D-p-hydrox...

Embodiment 3

[0027] In 80ml glacial acetic acid, add 8.5 grams (0.05mol) DL-p-hydroxyphenylglycine and 16.9 grams (0.05mol) (+)-3-bromo-8-ammonium camphorsulfonate, in N 2 Under the conditions of protection and stirring, the temperature was raised to 60°C, and after the formation of a white suspension, 2.5g (0.025mol) of sulfuric acid was slowly added dropwise. After the sulfuric acid was added dropwise, 0.24g of 2-nitro-benzaldehyde was added, and the reaction was carried out for 9 After one hour, the temperature was slowly lowered to 10° C., and the formed double salt was fully analyzed. Filter under reduced pressure to obtain 23.8 grams of white crystalline D-p-hydroxyphenylglycine (+)-3-bromo-8-camphorsulfonic acid double salt, the yield is 93.9%, after washing with a small amount of acetic acid, place in a vacuum oven Medium dry.

[0028] Take by weighing 23.8 grams of dry D-p-hydroxyphenylglycine · (+)-3-bromo-8-camphorsulfonic acid double salt, be dissolved in 58ml 50v / v% ethanol a...

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PUM

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Abstract

This invention relates to a preparation method of D - para hydroxybenzene glycine. It takes (+) - 3 - bromo-camphor ammonium sulphonate salt as resolution agent, under protection of 2 - nitryl - benzaldehyde and N2, split raceme para hydroxybenzene glycine to obtain D -glycine.

Description

technical field [0001] The invention relates to a preparation method of D-p-hydroxyphenylglycine, more specifically to a method for preparing high-purity D-p-hydroxyphenylglycine by splitting DL-p-hydroxyphenylglycine racemate through asymmetric conversion. Background technique [0002] p-Hydroxyphenylglycine is an amino acid prepared by chemical synthesis. Optically active p-hydroxyphenylglycine has important medical applications, and chiral p-hydroxyphenylglycine and its derivatives have broad application prospects in antimicrobial, antiviral and other fields. Among them, D-hydroxyphenylglycine can be used to synthesize broad-spectrum antibiotics such as amoxicillin, amoxicillin cephalosporin, cefoperazone, cefuroxime and cefadroxol, while L-p-hydroxyphenylglycine has auxiliary treatment for ischemic heart disease, The role of heart failure, diabetes and other diseases. The p-hydroxyphenylglycine synthesized by conventional methods is a racemate without chirality, and th...

Claims

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Application Information

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IPC IPC(8): C07C227/34C07C229/36
Inventor 伊汀朱春燕
Owner BAOSHAN IRON & STEEL CO LTD
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