Method of preparing D-p-hydroxyphenylglycine

A technology for p-hydroxyphenylglycine and naphthalene sulfonic acid is applied in the field of preparing high-purity D-p-hydroxyphenylglycine, which can solve the problems of low yield, long reaction time and the like, and achieves good quality, short reaction time and economical efficiency. cost reduction effect

Active Publication Date: 2009-07-29
INNER MONGOLIA CHANGSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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  • Method of preparing D-p-hydroxyphenylglycine

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Embodiment 1

[0017] Embodiment 1: the preparation method of the present invention comprises the following steps: (1), in 3000ml water, add 1030g DL-p-hydroxyphenylglycine (i.e. dexterous p-hydroxyphenylglycine) and 1350g resolution agent β-naphthalenesulfonic acid, be mixed with A solution with a concentration of about 44%. Under stirring conditions, the temperature was raised to 60°C for reaction, and a small amount of induced seed crystal (D-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt, 20g) was added to adjust the specific rotation value of the solution to 1.5°. Fully crystallized at 25°C, filtered under reduced pressure, and dried (in a vacuum oven) to obtain 1730 g of solid (white crystal) D-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt. The whole split time is 2.5 hours. The 1730g D-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt prepared in step (1) was dissolved in 1730g water, recrystallized and cooled to room temperature, and filter...

Embodiment 2

[0018] Embodiment 2: the preparation method of the present invention comprises the following steps: (1), in 3000ml water, add 1030g DL-p-hydroxyphenylglycine and 1350g resolving agent β-naphthalenesulfonic acid, be mixed with the solution that concentration is about 44%, in Under stirring conditions, heat up to 65°C for reaction, add a small amount of induced seed crystal (L-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt), adjust the specific rotation value of the solution to 1.7°, keep the reaction for 1.5 hours, and cool to 30°C Fully crystallized, filtered under reduced pressure and vacuum dried to obtain 1610 g of solid L-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt.

[0019] (1-1), the 1610g L-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt prepared in step (1) is dissolved in 2000g water, adds 5g benzaldehyde, is warming up to 120 ℃, racemization reaction (insulation 7 hours) until the optical rotation of L-p-hydroxyphenylgly...

Embodiment 3

[0021]Embodiment 3: the preparation method of the present invention takes β-naphthalenesulfonic acid as the resolving agent, resolves racemic DL-p-hydroxyphenylglycine, obtains D-p-hydroxyphenylglycine, and it comprises the steps: (1), in Add the DL-p-hydroxyphenylglycine and the resolving agent β-naphthalenesulfonic acid with a weight ratio of 1: 1.2 (or 1: 1.4 or 1: 1.6) in water, and prepare a concentration of 25% (or 35% or 45%) solution, heated up to 60°C (or 70°C or 80°C) under stirring conditions for reaction, adding induced seed crystals (D-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt) to adjust the specific rotation of the solution When the value reaches 1.5° (or 2.0°), heat preservation reaction for 1.4 hours, cool to 20°C (or 30°C or 40°C) to fully crystallize, filter and dry under reduced pressure to obtain solid D-p-hydroxyphenylglycine β-naphthalenesulfonic acid Double salt. (2), the D-p-hydroxyphenylglycine β-naphthalenesulfonic acid double sal...

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Abstract

A preparation method of D-p-hydroxyphenylglycine, which is to add DL-p-hydroxyphenylglycine and resolving agent β-naphthalenesulfonic acid in water to prepare a solution, raise the temperature under agitation to react, add induced seed crystals, and adjust the solution Specific rotation value, heat preservation reaction, cooling and sufficient crystallization, filtration under reduced pressure and drying to obtain solid D-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt or L-p-hydroxyphenylglycine β-naphthalenesulfonic acid double salt; D-p-Hydroxyphenylglycine β-naphthalenesulfonic acid double salt is dissolved in water to make an aqueous solution, heated up and added with activated carbon for decolorization, adjusted the pH value with lye, cooled to room temperature, filtered, washed and dried to obtain D-p-Hydroxyphenylglycine . The D-p-hydroxyphenylglycine produced by the invention has good quality, short reaction time and low cost.

Description

technical field [0001] The invention relates to a preparation method of D-p-hydroxyphenylglycine, and more particularly relates to a preparation method of high-purity D-p-hydroxyphenylglycine through a seed crystal induction method. Background technique [0002] p-Hydroxyphenylglycine is an amino acid prepared by chemical synthesis. Optically active D-p-hydroxyphenylglycine has important medicinal uses, and its chemical formula is as follows: [0003] [0004] As described in the background technology of CN101045693A, chiral D-p-hydroxyphenylglycine and its derivatives have broad application prospects in antimicrobial, antiviral and other fields. Among them, D-hydroxyphenylglycine can be used in the synthesis of broad-spectrum antibiotics such as amoxicillin, amoxicillin cephalosporin, cefoperazone, cefurozil, and cefadroxazole, while L-p-hydroxyphenylglycine has a role in the auxiliary treatment of ischemic heart disease. disease, heart failure, diabetes and other dise...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/36C07C227/34C07B57/00
Inventor 王国胜张士文桂胜光
Owner INNER MONGOLIA CHANGSHENG PHARMA
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