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A kind of synthetic method of tetronic acid

A synthesis method and a quaternary keto acid technology, applied in the direction of organic chemistry and the like, can solve the problems of long synthesis steps, dangerous and complicated process operation, and high synthesis cost, and achieve the effects of short synthesis steps, simple and convenient process operation and low synthesis cost.

Inactive Publication Date: 2016-04-27
UNIV OF SHANGHAI FOR SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a natural isovitamin C (also known as: D-isoascorbic acid) is a synthetic method for preparing tetronic acid as a starting material. The synthetic method has the advantages of simple synthesis process and easy operation, and the starting materials used in the synthesis process are cheap and easy to obtain, and the synthesis process does not need to use expensive noble metal catalysts. , so it also has the advantages of low synthesis cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of synthetic method of tetronic acid, specifically comprises the steps:

[0033] (1), preparation of erythrolide

[0034] Dissolve isovitamin C (17.6g, 0.1mol) in solvent (250mL), cool to 0°C, add sodium carbonate (21.2g, 0.2mol), then add hydrogen peroxide solution (46mL) with a concentration of 30% by volume , 0.45mmol), heated to 42°C and stirred for 30 minutes, then cooled to -10°C, added manganese dioxide (28.7g, 0.33mol), then heated to 60°C, and reacted under stirring until starch potassium iodide test paper Until no hydrogen peroxide remains in the test, the reaction ends and the reaction solution is obtained;

[0035] Described solvent is distilled water, and its consumption is calculated according to the ratio of isovitamin C: solvent is 1mol: 2.5L;

[0036] The used different vitamin C of above-mentioned reaction, sodium carbonate, volume percent concentration are the amount of 30% hydrogen peroxide aqueous solution and manganese dioxide, calculate b...

Embodiment 2

[0054] A kind of synthetic method of tetronic acid, specifically comprises the steps:

[0055] (1), preparation of erythrolide

[0056] Dissolve isovitamin C (17.6g, 0.1mol) in solvent (250mL), cool to 0°C, add sodium carbonate (21.2g, 0.2mol), then add hydrogen peroxide solution (46mL) with a concentration of 30% by volume , 0.45mmol), heated to 42°C and stirred for 30 minutes, then cooled to -10°C, added manganese dioxide (28.7g, 3.3mol), then heated to 60°C, and reacted under stirring until starch potassium iodide test paper Until no hydrogen peroxide remains in the test, the reaction ends and the reaction solution is obtained;

[0057] Described solvent is water, and its consumption is calculated according to the ratio of different vitamin C: solvent is 1mol: 2.5L;

[0058] The used different vitamin C of above-mentioned reaction, sodium carbonate, volume percent concentration are the amount of 30% hydrogen peroxide aqueous solution and manganese dioxide, calculate by mo...

Embodiment 3

[0076] A kind of synthetic method of tetronic acid, specifically comprises the steps:

[0077] (1), preparation of erythrolide

[0078] Dissolve isovitamin C (17.6g, 0.1mol) in solvent (250mL), cool to 0°C, add sodium carbonate (21.2g, 0.2mol), then add hydrogen peroxide solution (46mL) with a concentration of 30% by volume , 0.45mmol), heated to 42°C and stirred for 30 minutes, then cooled to -10°C, added manganese dioxide (28.7g, 3.3mol), then heated to 60°C, and reacted under stirring until starch potassium iodide test paper Until no hydrogen peroxide remains in the test, the reaction ends and the reaction solution is obtained;

[0079] Described solvent is distilled water, and its consumption is calculated according to the ratio of vitamin C: solvent is 1mol: 2.5L;

[0080] The used different vitamin C of above-mentioned reaction, sodium carbonate, volume percent concentration are the amount of 30% hydrogen peroxide aqueous solution and manganese dioxide, calculate by mo...

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Abstract

The invention discloses a synthetic method of tetronic acid. The synthetic method comprises the following steps: firstly oxidizing low-price easily-available natural sodium D-isoascorbate as a raw material through hydrogen peroxide, and acidifying through hydrochloric acid to prepare a key synthetic intermediate, namely erythronolactone; secondly, reacting erythronolactone with sulfonyl chloride to generate crude tetronic acid; finally, simply re-crystallizing obtained crude tetronic acid to obtain pure tetronic acid. The synthetic method has the characteristics of few synthetic steps, simple and convenient process, low synthetic cost, convenience for large-scale industrialized production and the like; finally obtained pure tetronic acid is high in yield and purity, the yield can reach more than 87%, and the purity can reach more than 99%.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a method for synthesizing tetronic acid, in particular to a method for synthesizing tetronic acid with natural chiral starting material isovitamin C (also known as: D-isoascorbic acid) as a chiral source resolve resolution. Background technique [0002] Tetronic acid, also known as tetronic acid, widely exists in natural products and has a variety of medicinal and biological activities. Its parent structure is 4-hydroxy-5H-furan-2-one, and its molecular formula is C 4 h 4 o 3 , the relative molecular weight is 100.02, the CAS number is 541-57-1, and the structural formula is as follows: [0003] . [0004] Based on the unique chemical structure of tetronic acid, it can be used as a starting material or a key synthetic intermediate for the synthesis of a series of chiral drugs (pharmaceuticals or pesticides). For example, tetronic acid can be used to synthesize wat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/60
CPCC07D307/60
Inventor 熊非李晓康沈中元王文强张淑平刘娅彭亚男朱海燕许明璐
Owner UNIV OF SHANGHAI FOR SCI & TECH
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