Method for separating and determining 1,2-propylene glycol enantiomers by using gas chromatography

A technology of gas chromatography and enantiomers, which is applied in the field of separation and determination of 1,2-propanediol enantiomers by pre-column derivatization gas chromatography, can solve the problems of inability to accurately quantify trace impurities and tailing, etc. Achieve the effects of improving tailing phenomenon, fast reaction speed and mild reaction conditions

Active Publication Date: 2016-07-06
CHONGQING PHARMA RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a method for the separation and determination of 1,2-propanediol enantiomers using pre-column derivatization gas chromatography, which overcomes the shortcomings of the prior art, that is, 1,2-propanediol is used in commonly used During the separation process of chiral gas chromatography column, there are technical defects that the peaks are seriously tailed and trace impurities cannot be accurately quantified

Method used

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  • Method for separating and determining 1,2-propylene glycol enantiomers by using gas chromatography
  • Method for separating and determining 1,2-propylene glycol enantiomers by using gas chromatography
  • Method for separating and determining 1,2-propylene glycol enantiomers by using gas chromatography

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Embodiment 1

[0034] Instruments and Conditions

[0035] Shimadzu gas chromatograph (GC-2010) and LabSolutions workstation; automatic sample injection; CD-Chirasil-DEXCB (0.25 μm, 25m×0.25 μm) as the analytical column; the detector is a hydrogen flame ion detector; the initial temperature is 60 ℃, maintained for 10 minutes, raised to 150 ℃ at a rate of 40 ℃ per minute, and maintained for 5 minutes; the temperature of the injection port was 250 ℃, and the split ratio was 50:1; the temperature of the detector was 250 ℃; the carrier gas was nitrogen, and the flow rate was It is 1.0ml per minute, and the injection volume is 1ml.

[0036] Experimental procedure

[0037] Precisely measure 5ml of acetone and put it into a microreactor, add 0.5g of water remover (4A molecular sieve) and 10mg of catalyst (Amberlyst-15), seal it, stir at room temperature for 1h, take the reaction solution and filter it with 0.45μm, and the filtrate is used as the test sample solution. Get need testing solution and...

Embodiment 2

[0042] Take about 100mg of (R)-1,2-propanediol, accurately weigh it, put it in a 10ml measuring bottle, add acetone to dissolve and dilute to the mark, shake well, accurately measure 5ml and place it in a microreactor, add a water remover (4A Molecular sieve) 0.5g and catalyst (Amberlyst-15) 10mg, seal, stir at room temperature for 1h, take the reaction solution and filter it with 0.45μm, and the filtrate is used as the test solution. Get need testing solution and carry out gas chromatograph analysis under above-mentioned conditions, the results are shown in Figure 5 ; The results of the determination of (S)-1,2-propanediol by the same method are shown in Figure 6 .

[0043] Figure 5 The chromatographic peaks with retention times of 6.0 minutes and 7.0 minutes are (R)-1,2-propanediol derivatives and their enantiomer impurities (S)-1,2-propanediol derivatives (impurity content: 0.96%), respectively. Figure 6 The chromatographic peaks at 6.6 minutes and 6.4 minutes were (...

Embodiment 3

[0045] Take about 0.5g of dapagliflozin raw material (approximately equivalent to (S)-1,2-propanediol 90mg), weigh it accurately, put it in a 10ml measuring bottle, add acetone to dissolve and dilute to the mark, shake well, and measure it precisely Put 5ml into a microreactor, add 0.5g of water remover (4A molecular sieve) and 20mg of catalyst (Amberlyst-15), seal it, stir at room temperature for 1h, take the reaction solution and filter it with 0.45μm, and the filtrate is used as the test solution; (R)-1,2-propanediol reference substance is about 10mg, accurately weighed, put in a 10ml measuring bottle, add acetone to dissolve and dilute to the mark, shake well, accurately measure 5ml and put it in a micro reactor, add a water remover ( 4A molecular sieve) 0.5g and catalyst (Amberlyst-15) 20mg, seal, stir at room temperature for 1h, take the reaction solution and filter it with 0.45μm, accurately measure 1ml of the subsequent filtrate, put it in a 100ml measuring bottle, dilu...

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Abstract

The invention discloses a method for separating and determining 1,2-propylene glycol, bulk drugs containing 1,2-propylene glycol and 1,2-propylene glycol enantiomer impurities in preparations of the bulk drugs by using precolumn derivatization gas chromatography. The method employs an aldehyde ketone compound as a derivative reagent, carries out precolumn derivatization on the aldehyde ketone compound and 1,2-propylene glycol in the presence of a catalyst and a water reducer and determines trace enantiomer impurities by using gas chromatography. The method provided by the invention overcomes the defect of incapability of accurate quantification of 1,2-propylene glycol enantiomer impurities due to serious trailing of peaks during frequently-used chiral gas chromatographic column separation and guarantees that the quality of 1,2-propylene glycol, the bulk drugs containing 1,2-propylene glycol and the preparations thereof is controllable.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and in particular relates to a method for separating and measuring 1,2-propanediol enantiomers by using pre-column derivatization gas chromatography. Background technique [0002] Dapagliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor jointly developed by AstraZeneca and Bristol-Myers Squibb. Its molecular formula is C 21 h 25 ClO 6 , its chemical name is: (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol and ( 2s) Hydrate of -1,2-propanediol. Since dapagliflozin exists in the form of (2s)-1,2-propanediol hydrate, another enantiomer of propylene glycol (2R)-1,2-propanediol will be introduced during the synthesis of the compound , the product contains (2R)-1,2-propanediol impurity. Therefore, it is necessary to control the content of the impurity (2R)-1,2-propanediol in the Dapagliflozin product, and carry out type-testing and analysis. The raw mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/06
Inventor 王娅温晓静白晓虹张道林谢峰雷皇书
Owner CHONGQING PHARMA RES INST
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