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, an

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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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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