Ester exchange method synthesizing process of aryl acetic acid (propionic acid) L-ascorbic acid ester

A technology for ascorbic acid ester and synthesis process, which is applied in the field of transesterification synthesis process of arylacetic acid L-ascorbic acid ester, and can solve problems such as waste of raw materials and environmental pollution

Inactive Publication Date: 2012-12-19
JIANGNAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Secondly, in the existing preparation process, saturated brine is used to wash the filtrate in the separation and extraction step,

Method used

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  • Ester exchange method synthesizing process of aryl acetic acid (propionic acid) L-ascorbic acid ester
  • Ester exchange method synthesizing process of aryl acetic acid (propionic acid) L-ascorbic acid ester
  • Ester exchange method synthesizing process of aryl acetic acid (propionic acid) L-ascorbic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1, L-ascorbic acid-6-O-ibuprofen ester

[0017]

[0018] In a 250 mL three-necked flask, add 5 g of L-ascorbic acid and 100 mL of 20% (w / v) ibuprofen methyl ester-tert-butanol solution, and heat to 55° C. in a water bath. Then add 1g of Novozym435, stir the reaction, turn on the vacuum pump after 12hrs of reaction, and keep the vacuum at 0.03-0.04MPa to distill the generated methanol. After reacting for 24 hrs, a reaction mixture was obtained.

[0019] Filtrate while hot to remove unreacted reactants and enzymes to obtain a clear filtrate. The filtrate was rotary-evaporated under reduced pressure to recover tert-butanol, and the obtained mixture was weighed, and cyclohexane was added in an amount of 10%, slightly heated in a water bath at 45°C, fully stirred to dissolve, and crystallized by cooling at room temperature. Filter, wash the filter cake with cyclohexane several times, recover the filter cake, and dry the filter cake at room temperature. The o...

Embodiment 2

[0022] Embodiment 2, L-ascorbic acid-6-O-(S)-ibuprofen ester

[0023]

[0024] The method is the same as that used in Example 1, except that (S)-ibuprofen methyl ester is used instead of racemic ibuprofen methyl ester to obtain L-ascorbic acid-6-O-(S)-ibuprofen ester.

[0025] The L-ascorbic acid-6-O-(S)-ibuprofen ester is tested by liquid phase-mass spectrometry, and the purity of the product is >98%.

[0026] L-ascorbic acid is recovered and recycled in the next round of reaction.

Embodiment 3

[0027] Embodiment 3, L-ascorbic acid-6-O-ketoprofen axetil

[0028]

[0029] In a 250 mL three-necked flask, add 10 g (0.57 mol) of L-ascorbic acid and 100 mL of 25% (w / v) ketoprofen ethyl ester-tert-amyl alcohol solution, and heat to 55° C. in a water bath. Then add 1g of Novozym435, stir the reaction, turn on the vacuum pump after 12hrs of reaction, and keep the vacuum at 0.04-0.05MPa to evaporate the ethanol generated. After reacting for 24 hrs, a reaction mixture was obtained.

[0030] Filtrate while hot to remove unreacted reactants and enzymes to obtain a clear filtrate. The filtrate was rotary evaporated under reduced pressure to recover tert-amyl alcohol, the resulting mixture was weighed, and cyclohexane was added in an amount of 5%, slightly heated on a 45°C water bath, fully stirred to dissolve, and cooled to crystallize at room temperature. Filter, wash the filter cake with cyclohexane several times, recover the filter cake, and dry the filter cake at room tem...

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Abstract

The invention belongs to the field of nonaqueous phase enzymatic organic synthesis, in particular to an ester exchange method synthesizing process of aryl acetic acid (propionic acid) L-ascorbic acid ester. The process is applicable to synthesis of the aryl acetic acid (propionic acid) L-ascorbic acid ester under catalysis of a biocatalyst (such as Novozym 435). The synthesizing process provides a commonly-used synthesizing process of the aryl acetic acid (propionic acid) L-ascorbic acid ester, can move to a ester synthesizing direction in balance through decompression and continuous alcohol removal on premises of influencing no catalytic activity of the biocatalyst, accordingly improves conversion rate of the enzymatic organic synthesis and guarantees reaction to trend to completion. Through simulated moving bed chromatography separation, through separation of reaction products and excess reaction raw materials are guaranteed, circulation and reuse problems of the excess reaction raw materials are solved, the conversion rate, product yield and product purity of the raw materials are all improved to be close to 100%, cost of production is substantially lowered, zero discharge of waste water and waste residues of product production is achieved, and the synthesizing process has wide application prospects in fields such as medicines and fine chemical engineering.

Description

technical field [0001] The invention belongs to the field of non-aqueous phase enzymatic organic synthesis, in particular to a synthesis process of transesterification of aryl ethyl (propion) acid L-ascorbyl ester. Background technique [0002] The aryl ethyl (propion) acid non-steroidal anti-inflammatory analgesics represented by ibuprofen has good anti-inflammatory, analgesic and antipyretic effects, good safety, and less adverse reactions. It has been used in the world at present. widely used. However, such drugs generally have disadvantages such as poor water solubility, irritating the gastrointestinal tract, and slow absorption, which also bring a lot of inconvenience to children, the elderly, and patients who cannot swallow solid preparations. [0003] Aryl ethyl (propion) acid L-ascorbyl ester [1] improves the shortcomings of aryl ethyl (propion) acid non-steroidal anti-inflammatory analgesics, has good solubility, high bioavailability, and rapid onset of action Val...

Claims

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Application Information

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IPC IPC(8): C12P17/04C07D307/62C07D491/052C07D405/12
CPCY02P20/54Y02P20/584
Inventor 汤鲁宏曹雅晴
Owner JIANGNAN UNIV
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