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Splitting method for racemic 2-benzene propanoic acid

A technology for phenylpropionic acid and racemization, applied in the field of separating L-2-phenylpropionic acid and D-2-phenylpropionic acid

Inactive Publication Date: 2013-05-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the field of separation science, chromatographic resolution is one of the important means of chiral separation, in which the classical liquid chromatography resolution technology occupies a dominant position, but this technology usually requires expensive chiral columns and is only suitable for very high added value enantiomeric separation

Method used

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  • Splitting method for racemic 2-benzene propanoic acid
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  • Splitting method for racemic 2-benzene propanoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Mix n-hexane: ethyl acetate: phosphate buffer containing hydroxypropyl-β-cyclodextrin (prepared with 0.1mol / L phosphate buffer solution, pH=2.6, containing 0.1mol / L hydroxypropyl -β-cyclodextrin, with a substitution degree of 7.5) was configured in a separatory funnel at a volume ratio of 5:5:10, shaken up and allowed to stand to separate layers. After equilibrating for a period of time, the upper and lower phases were separated, the organic phase was used as the stationary phase, and the aqueous phase was used as the mobile phase.

[0041] (2) Weigh 40 mg of racemic 2-phenylpropanoic acid and dissolve it in 6 ml of water phase, and make a sample solution after dissolving for use.

[0042] (3) Use a semi-preparative high-speed countercurrent chromatograph (Shanghai Tongtian Biotechnology Co., Ltd., instrument model TBE-300A) to resolve racemic 2-phenylpropionic acid: the volume of the separation column is 300ml, and the countercurrent chromatographic The separation...

Embodiment 2

[0045] (1) Mix n-hexane: ethyl acetate: phosphate buffer containing hydroxypropyl-β-cyclodextrin (prepared with 0.1mol / L phosphate buffer solution, pH=2.6, containing 0.1mol / L hydroxypropyl -β-cyclodextrin, the degree of substitution is 7.5) was configured in a separating funnel according to the volume ratio of 8:2:10, shake well and then stand to separate layers. After equilibrating for a period of time, the upper and lower phases were separated, the organic phase was used as the stationary phase, and the aqueous phase was used as the mobile phase.

[0046] (2) Weigh 40 mg of racemic 2-phenylpropanoic acid and dissolve it in 6 ml of water phase, and make a sample solution after dissolving for use.

[0047] (3) Use a semi-preparative high-speed countercurrent chromatograph (Shanghai Tongtian Biotechnology Co., Ltd., instrument model TBE-300A) to resolve racemic 2-phenylpropionic acid: the volume of the separation column is 300ml, and the countercurrent chromatographic The sep...

Embodiment 3

[0050] (1) Mix n-hexane: ethyl acetate: phosphate buffer containing hydroxypropyl-β-cyclodextrin (prepared with 0.1mol / L phosphate buffer solution, pH=3.2, containing 0.1mol / L hydroxypropyl -β-cyclodextrin, degree of substitution 7.5) was configured in a separatory funnel at a volume ratio of 5:5:10, shaken well and allowed to stand to separate layers. After equilibrating for a period of time, the upper and lower phases were separated, the organic phase was used as the stationary phase, and the aqueous phase was used as the mobile phase.

[0051] (2) Weigh 40mg of racemic 2-phenylpropionic acid and dissolve it in 6ml of water phase, and make a sample solution after dissolution.

[0052] (3) Use a semi-preparative high-speed countercurrent chromatograph (Shanghai Tongtian Biotechnology Co., Ltd., instrument model TBE-300A) to resolve racemic 2-phenylpropionic acid, and the volume of the separation column is 300ml. Before sample injection, the countercurrent chromatographic sep...

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Abstract

The invention discloses a splitting method for racemic 2-benzene propanoic acid. The splitting method comprises the following steps: using an organic solvent A, an organic solvent B and a phosphate buffer solution containing hydroxypropyl-beta-cyclodextrin to constitute a solvent system according to the volume ratio of 1-8: 2-6: 10, uniformly mixing, and standing for stratification to get an organic phase and a water phase; dissolving racemic 2-benzene propanoic acid with the obtained water phase to prepare a sample; and splitting racemic 2-benzene propanoic acid by adopting high-speed counter-current chromatography, separating a prepeak eluate and a postpeak eluate, and recovering to get levo-2-benzene propanoic acid monomer and dextro-2-benzene propanoic acid monomer. By adopting the method disclosed by the invention to split racemic 2-benzene propanoic acid, the higher separation degree can be achieved; and the method is further suitable for various types of preparation type counter-current chromatographic instruments, and the levo-2-benzene propanoic acid monomer and the dextro-2-benzene propanoic acid monomer can be obtained by separation.

Description

(1) Technical field [0001] The invention relates to a method for separating L-2-phenylpropionic acid and D-2-phenylpropionic acid from racemic 2-phenylpropionic acid. (2) Background technology [0002] 2-phenylpropionic acid (2-PPA) is an important intermediate and fine chemical product of arylpropionic acid anti-inflammatory and analgesic drugs, which can be used to synthesize chiral drugs such as soronofin calcium. Optically active 2-phenylpropionic acid is a very important non-steroidal anti-inflammatory drug, and the anti-inflammatory components mainly exist in the S-isomer. Therefore, it is a subject of theoretical and practical significance to study the chiral resolution of racemic 2-phenylpropionic acid and to establish a fast and good separation method for the resolution of racemic 2-phenylpropionic acid. At present, there are few methods for preparing and resolving racemic 2-phenylpropionic acid, mainly high-performance liquid chromatography and chiral solvent extr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/47C07C57/30
Inventor 颜继忠童胜强郑烨
Owner ZHEJIANG UNIV OF TECH
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