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High performance liquid chromatography splitting method for Boc hydroxyl adamantane amino acid

A high-performance liquid chromatography and amino acid technology, which is applied in the field of high-performance liquid chromatography of Boc hydroxyadamantane amino acid, can solve the problems that the enantiomeric impurity content cannot be measured, there is no S-Boc hydroxyadamantane amino acid, etc., and achieve Solve quality control problems, strong practical effect

Inactive Publication Date: 2014-07-09
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the close properties of optical isomers, the main detection methods of chiral enantiomers are optical rotation and high performance liquid chromatography. Since there is no commercially available standard for S-Boc hydroxyadamantane amino acid, and optical rotation cannot Determination of the content of its enantiomeric impurities
Through literature search, there is no relevant literature report on the detection of S-Boc hydroxyadamantane amino acid and its enantiomer

Method used

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  • High performance liquid chromatography splitting method for Boc hydroxyl adamantane amino acid
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  • High performance liquid chromatography splitting method for Boc hydroxyl adamantane amino acid

Examples

Experimental program
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Embodiment 1

[0034] A high performance liquid chromatography resolution method for Boc-hydroxyadamantane amino acid, the steps are as follows:

[0035] Take 20 mg of Boc-hydroxyadamantane amino acid, put it in a 10 mL volumetric flask, add ethanol to dissolve, add n-hexane to dissolve and dilute to the mark, as the sample solution to be tested, and take n-hexane-ethanol blank solution as a control;

[0036] That is, high-performance liquid chromatography is used, with amylose-type chiral column, that is, coated chiral chromatographic column CHIRALPAK AD-H as the chromatographic column, and a mixed solution composed of n-hexane and ethanol as the mobile phase, and the following chromatographic separation is adopted condition to separate:

[0037] The mobile phase flow rate is 1.0 mL / min;

[0038] The temperature of the chromatographic column is 35°C;

[0039] The injection volume is 15 uL;

[0040] The detection wavelength is 220 nm;

[0041] In the mobile phase, calculated by volume pe...

Embodiment 2

[0044] A high performance liquid chromatography resolution method for Boc-hydroxyadamantane amino acid, the steps are as follows:

[0045] Take 20 mg of Boc-hydroxyadamantane amino acid, put it in a 10 mL volumetric flask, add ethanol to dissolve, add n-hexane to dissolve and dilute to the mark, as the sample solution to be tested, and take n-hexane-ethanol blank solution as a control;

[0046]That is, high-performance liquid chromatography is used, with amylose-type chiral column, that is, coated chiral chromatographic column CHIRALPAK AD-H as the chromatographic column, and a mixed solution composed of n-hexane and ethanol as the mobile phase, and the following chromatographic separation is adopted condition to separate:

[0047] The mobile phase flow rate is 1.0 mL / min;

[0048] The temperature of the chromatographic column is 35°C;

[0049] The injection volume is 15 uL;

[0050] The detection wavelength is 220 nm;

[0051] In the mobile phase, calculated by volume per...

Embodiment 3

[0054] A high performance liquid chromatography resolution method for Boc-hydroxyadamantane amino acid, the steps are as follows:

[0055] Take 20 mg of Boc-hydroxyadamantane amino acid, put it in a 10 mL volumetric flask, add ethanol to dissolve, add n-hexane to dissolve and dilute to the mark, as the sample solution to be tested, and take n-hexane-ethanol blank solution as a control;

[0056] That is, high-performance liquid chromatography is used, with amylose-type chiral column, that is, coated chiral chromatographic column CHIRALPAK AD-H as the chromatographic column, and a mixed solution composed of n-hexane and ethanol as the mobile phase, and the following chromatographic separation is adopted condition to separate:

[0057] The mobile phase flow rate is 1.0 mL / min;

[0058] The temperature of the chromatographic column is 35°C;

[0059] The injection volume is 15 uL;

[0060] The detection wavelength is 220 nm;

[0061] In the mobile phase, calculated by volume pe...

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Abstract

The invention discloses a high performance liquid chromatography splitting method for Boc hydroxyl adamantane amino acid. A high performance liquid chromatograph is adopted, a straight-chain starch type chiral column is used as a chromatographic column, and mixed liquid of normal hexane and ethyl alcohol or normal hexane and isopropanol is used as a flowing phase; the flowing speed of the flowing phase is controlled to be 0.60-1.20 mL / min; chromatographic separation is performed under conditions that the temperature of the chromatographic column is 25-40 DEG C, the sample injection amount is 5-20 microliters, and the detection wavelength is 210-260 nm; according to the volume percentage, a ratio of the normal hexane to the ethyl alcohol (or isopropanol) is (70-90 percent):(10-30 percent). Separation and measurement of the R and S type Boc hydroxyl adamantane amino acid in a Boc-hydroxyl adamantane amino acid despinner are effectively realized, and the separation degree is up to 3.25-4.57.

Description

technical field [0001] The invention belongs to the field of drug analysis and detection, and relates to a high performance liquid chromatography resolution method for Boc hydroxyadamantane amino acid. Background technique [0002] The chemical name of Saxagliptin (Saxagliptin, trade name OnglyzaTM) is (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]decane -1-yl) acetyl] -2- azabicyclo [3.1.0] hexane -3-carbonitrile, saxagliptin), the molecular formula is C 18 h 25 N 3 o 2 . The drug is chiral, and the structural formula of saxagliptin is as follows: [0003] [0004] According to the literature report of saxagliptin, the synthesis of saxagliptin is obtained through two intermediates of unnatural α-chiral amino acid derivatives and chiral cyclopropane three-membered ring: intermediate A (S-(3-hydroxy -1-adamantane)-2-(tert-butoxycarbonylamino)acetic acid, and intermediate B ((1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide) specifically As follows: ...

Claims

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Application Information

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IPC IPC(8): G01N30/02
Inventor 潘仙华徐娜于一文刘圣江闫茜史尧赵东贤陈思羽张瑞敏李晓军丁丁白书培王琨徐斯尧
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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