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Method for preparing DL-isoserine

A technology of isoserine and acrylic acid, which is applied in the field of preparation of chiral organic compounds, can solve the problem of high cost, and achieve the effects of low environmental pollution, cheap and easy-to-obtain reaction raw materials, and high selectivity

Inactive Publication Date: 2014-07-30
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method avoids the use of sodium azide and reduces environmental pollution, but the relatively expensive raw materials nitromethane and glyoxylic acid are still used in the reaction, and the reduction of nitro groups is also involved, so the cost of industrialization is relatively high

Method used

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  • Method for preparing DL-isoserine

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Effect test

example 1

[0016] Add 5mL (0.077mol) of acrylic acid and 10mL of distilled water into a 100mL three-necked flask equipped with a magnetic stirrer. mL (0.077mol) of tert-butyl hypochlorite, after the dropwise addition, was concentrated in vacuo at 40°C to obtain 4.5 mL of oily liquid α-chloro-β-hydroxypropionic acid. Add 50mL of concentrated ammonia water to a 250mL three-necked flask equipped with a magnetic stirrer, and slowly add the above oily liquid dropwise under the condition of an ice-salt bath. Reflux for 1 h, filter, dry, recrystallize with water and ethanol, filter, and dry to obtain 5.66 g of DL-isoserine as a white powder, m.p.

example 2

[0018] Add 50mL (0.77mol) of acrylic acid and 100mL of distilled water into a 100mL three-neck flask equipped with a magnetic stirrer. The volume ratio is: acrylic acid: water = 1:2. Use an ice-salt bath to control the reaction temperature at about 0°C, and slowly add 92mL of (0.77mol) tert-butyl hypochlorite, after the dropwise addition, concentrated in vacuo at 40°C to obtain 4 mL of oily liquid α-chloro-β-hydroxypropionic acid. Add 500mL of concentrated ammonia water into a 1L three-necked flask equipped with a magnetic stirrer, and slowly add the above oily liquid dropwise under the condition of an ice-salt bath. Reflux for 1 hour, filter, dry, recrystallize with water and ethanol, filter, and dry to obtain 52.6 g of DL-isoserine as white powder, m.p.242-244°C, yield 65%.

example 3

[0020] Add 5mL (0.077mol) of acrylic acid and 60mL of distilled water into a 100mL three-necked flask equipped with a magnetic stirrer, and add 6.85g of NBS in batches at 20°C. After the reaction is complete, extract the reaction solution with ether three times, combine the extracts, and vacuum Ether was removed to obtain 4.5 mL of oily α-bromo-β-hydroxypropionic acid. Ammonolysis of the obtained α-bromo-β-hydroxypropionic acid is performed with the ammonolysis part of Example 1. The obtained crude product was refluxed with absolute ethanol, recrystallized with water and ethanol, and decolorized with activated carbon, filtered, left to stand overnight in the refrigerator, filtered, and dried to obtain 5.5 g of DL-isoserine in white powder form, with a total yield of 68 % (based on starting material acrylic acid).

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Abstract

The invention discloses a method for preparing DL-isoserine. The preparation method specifically comprises the following steps: with acrylic acid as a raw material, adding distilled water with the volume ratio of acrylic acid to water being 1: (1 to 15), and preparing alpha-X-beta-hydracrylic acid, wherein X is Cl or Br; in a condition of 30-80 DEG C, dripping the prepared alpha-X-beta-hydracrylic acid in commercially available stronger ammonia water with the volume ratio of the alpha-X-beta-hydracrylic acid to the stronger ammonia water being 1: (5 to 20), reacting for 5-20 hours, carrying out vacuum concentration to dryness, refluxing for 1-3 hours by absolute methanol, filtering, drying, recrystallizing by water and ethanol, filtering, and drying to obtain the white powder DL-isoserine. The process is simple in steps, few in side reactions, low in pollution and low in cost and has an industrial application prospect.

Description

technical field [0001] The invention is a method for preparing chiral organic compounds, especially a method for preparing DL-isoserine. Background technique [0002] With the long-term and extensive use of drugs, drug resistance will inevitably occur, reducing the efficacy of drugs. Research and development of new drugs by modifying the structure of original drugs is one of the common methods for people to develop new drugs. Adding amino acid side chains to the drug molecule can significantly improve the efficacy of the drug, such as amoxicillin, amikacin, amikacin, etc. The introduction of amino acids into anti-tumor drug molecules can improve its selectivity for tumor cells, enhance the fat solubility of drugs, and alleviate the toxicity of drugs to cells, such as amino acid derivatives containing 5-fluorouracil, β-germanium-α-amino acids Derivatives, so amino acids play an important role in biological research and drug synthesis. β-Amino acid is a class of chiral inte...

Claims

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Application Information

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IPC IPC(8): C07C227/08C07C229/22
Inventor 蒋立建何慧付倩倩唐赛杰顾美萍
Owner SOUTHEAST UNIV
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