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Separation and detection method and application of 3-chlorophenylpropanol optical isomers

A technology for optical isomers and detection methods, applied in the field of analysis, can solve problems such as liquid phase, large damage to the chromatographic column, severe tailing, and poor resolution

Active Publication Date: 2018-02-02
REGENEX PHARMA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Optical polarimetry cannot accurately detect the content of isomers; Xu Jiangyan applied a Diace OD-H chiral column as a chromatographic column, and used n-hexane and isopropanol as mobile phases for high performance liquid chromatography to determine (S)- Content of optical isomers of (-)-3-chloro-1-phenyl-1-propanol [Biological preparation of (S)-3-chloro-1-phenylpropanol [D], Zhejiang University of Technology, 2009 ]; Gong Dachun and others used similar chromatographic conditions to determine the optical purity of (R)-(+)-3-chloro-1-phenyl-1-propanol [immobilized lipase catalyzed synthesis of (R)-3-chloro-1 -Phenylpropanol [J], Chinese Journal of Pharmaceutical Industry, 2007, No. 11], the above-mentioned methods are all normal phase chromatographic systems, and the method has poor reproducibility, severe tailing, and poor resolution. Liquid phase, chromatographic column, etc. are more damaged, and the mobile phase used is more expensive

Method used

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  • Separation and detection method and application of 3-chlorophenylpropanol optical isomers
  • Separation and detection method and application of 3-chlorophenylpropanol optical isomers
  • Separation and detection method and application of 3-chlorophenylpropanol optical isomers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Instruments and Conditions

[0019] Instrument: Shimadzu LC-20A high performance liquid chromatograph, electronic analytical balance

[0020] Chromatographic column: CHURALCEL AGP 150 x 4mm, 5μm

[0021] Column temperature: 25°C

[0022] UV detection wavelength: 210nm

[0023] Mobile Phase: Water: Acetonitrile (92:8)

[0024] Flow rate: 0.30ml / min

[0025] System Suitability Test

[0026] Experimental procedure

[0027] Weigh 10 mg of (S)-(-)-3-chloro-1-phenyl-1-propanol reference substance (batch number: 201401201, Guangzhou Langsheng Pharmaceutical Co., Ltd.), put it in a 50ml volumetric flask, and add an appropriate amount of mobile phase Dissolve and dilute to the mark, shake well, as (S)-3-chloro-1-phenylpropanol positioning solution; weigh (R)-(+)-3-chloro-1-phenyl-1-propanol Reference substance (batch number: 201401202, Guangzhou Langsheng Pharmaceutical Co., Ltd.) 10mg

[0028] , configured in the same way as (R)-3-chloro-1-phenylpropanol positioning sol...

Embodiment 2

[0054] Instruments and Conditions

[0055] Instrument: Shimadzu LC-20A high performance liquid chromatograph, electronic analytical balance

[0056] Chromatographic column: chiral AGP 100 x 4mm, 5μm

[0057] Column temperature: 15°C

[0058] UV detection wavelength: 215nm

[0059] Mobile Phase: Water: Acetonitrile (92:8)

[0060] Flow rate: 0.30ml / min

[0061] experiment procedure

[0062] Inject 10 μl of the system suitability solution configured in Example 1, (S)-3-chloro-1-phenylpropanol test solution and (R)-3-chloro-1-phenylpropanol respectively according to the above chromatographic conditions Alcohol test solution.

Embodiment 3

[0064] Instruments and Conditions

[0065] Instrument: Shimadzu LC-20A high performance liquid chromatograph, electronic analytical balance

[0066] Chromatographic column: CHURALCEL AGP 150 x 4mm, 5μm

[0067] Column temperature: 25°C

[0068] UV detection wavelength: 210nm

[0069] Mobile Phase: Water: Acetonitrile (84:16)

[0070] Flow rate: 0.30ml / min

[0071] experiment procedure

[0072] Inject 10 μl of the system suitability solution configured in Example 1, (S)-3-chloro-1-phenylpropanol test solution and (R)-3-chloro-1-phenylpropanol respectively according to the above chromatographic conditions Alcohol test solution.

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Abstract

A separating and detecting method for 3-chloro-1-phenyl-1-propanol optical isomers is disclosed. The method is high efficiency liquid chromatography. According to chromatographic conditions of the method, an alpha-acid glycoprotein (AGP) bonded chiral chromatographic column is adopted, a solvent mixture of water and acetonitrile is adopted as a mobile phase, the volume ratio of the water to the acetonitrile is 84-98:16-2, an ultraviolet detector is adopted for detection, a flow rate is 0.15-0.7 mL / min, and the column temperature of the chromatographic column is 15-45 DEG C. The method is simple and convenient in operation, high in sensitivity, good in separation degree, accurate and reliable in results and low in detection cost.

Description

technical field [0001] The invention belongs to the technical field of analysis, and in particular relates to a method for separating and detecting optical isomers of 3-chlorophenylpropanol and an application thereof. Background technique [0002] Chiral halogen-containing aryl alcohols are very important compounds in chiral synthesis, and 3-chlorophenylpropanol is a typical representative. There is a chiral center in the 3-chlorophenylpropanol molecule, and there are two optical isomers, namely (S)-(-)-3-chloro-1-phenyl-1-propanol and (R)-( +)-3-chloro-1-phenyl-1-propanol, its structural formula is shown in formula I and formula II respectively: [0003] (formula Ⅰ) (Formula II) [0004] (S)-(-)-3-Chloro-1-phenyl-1-propanol is a key intermediate for the chiral synthesis of serotonin reuptake blockers such as atomoxetine and fluoxetine【CoreyE.J ., Reiehard GregoyrA., Ennatioseletive and Practiealsynthesis of R-and S- Fluoxetine, Tetrahedron Lettesr, 1989, 30(39):5207-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N30/02
Inventor 高曙光杨艳汤丹袁永玲彭贵子左联卢智俊
Owner REGENEX PHARMA LTD