CN107677735A - A kind of HPLC analysis methods of (S) 2 aminopropanol - Google Patents
A kind of HPLC analysis methods of (S) 2 aminopropanol Download PDFInfo
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- CN107677735A CN107677735A CN201610620357.9A CN201610620357A CN107677735A CN 107677735 A CN107677735 A CN 107677735A CN 201610620357 A CN201610620357 A CN 201610620357A CN 107677735 A CN107677735 A CN 107677735A
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- aminopropanols
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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Abstract
Present invention relates particularly to a kind of detection method of (S) 2 aminopropanol chiral purity, the present invention uses 2, 3, 4, 5 tetrafluorobenzoic aid acetic anhydrides are that derivative reagent carries out quick derivatization generation (S) 2 with (S) 2 aminopropanol in room temperature and methanol solvate, 3, 4, 5 tetrafluoro N (base of 1 hydroxyl 2) benzamide, then tested and analyzed using HPLC UV, under the process conditions, (S) 2 aminopropanol derivatives and the derivative of its enantiomter are efficiently separated, methodology result meets analysis measure and required, it is fast and reliable, it is simple to operate, favorable reproducibility, high sensitivity.
Description
Technical field
The invention belongs to Pharmaceutical Analysis technical field, and in particular to the high-efficient liquid phase color of (S) -2- aminopropanol chiral purities
Spectral analysis method.
Background technology
(S) -2- aminopropanols (III) are the important intermediates for synthesizing lavo-ofloxacin, and lavo-ofloxacin is Ofloxacin
S types do rotation optical isomer, antibacterial activity is twice of the latter, and toxic side effect is small, water-soluble big, except peroral dosage form
Outside, injection type can also be made.(S) quality of -2- aminopropanols, particularly chiral purity quality, directly affect a left side
The quality of Ofloxacin, therefore chiral detection method is whether accurate extremely important, at present, the country does not have (S) -2- aminopropanols
The relevant report of chirality detection, (S) -2- aminopropanols and its chiral isomer UV absorption are very weak, therefore generally use derives
Change method is allowed to UV absorption enhancing so as to improve detection sensitivity, while uses suitable derivatization reagent and chromatographic condition,
It is the underlying issue for being badly in need of solving that detection can be made, which to complete measure in a short period of time,.The present invention is based on such purpose and entered
Go and studied and provide a kind of quick assay method.
The content of the invention
In order to make up the domestic blank without measure (S) -2- aminopropanol chiral purity methods, the present invention uses efficient liquid
Phase chromatography establishes the inspection assay method of (S) -2- aminopropanol chiral purities, can preferably control (S) -2- aminopropanols
Chirality, it is ensured that product quality, the present invention, which relates to, to be comprised the following steps：
Step 1, derivatization
By (S) -2- aminopropanols, at ambient temperature, with 2,3,4,5- tetrafluorobenzoic aid acetic anhydrides for derivatization reagent, adjust
(S) -2- aminopropanols and 2, the mol ratio of 3,4,5- tetrafluorobenzoic aid acetic anhydrides, perform the derivatization and react generation (S) -2,3,4,
Tetra- fluoro- N- of 5- (1- hydroxyl -2- bases) benzamide (I)；
Step 2, HPLC analyses
Using RPLC-ultraviolet spectra detector to four fluoro- N- of (S) -2,3,4,5- (1- hydroxyl -2- bases) benzene
Formamide carries out enantiomeric excess rate analysis, and then obtains to (S) -2- aminopropanol enantiomeric excess rate data；
Preferably, the organic solvent of dilution derivative reagent is selected from group more than one or both of methanol, toluene, dichloromethane
Close.
Preferably, (the S) -2- aminopropanols and 2, the mol ratio of 3,4,5- tetrafluorobenzoic aid acetic anhydrides is 1:0.5~1:
1。
Preferably, it is 10 DEG C ~ 30 DEG C to refer to range of reaction temperature under the room temperature condition；Preferably temperature range is 20 DEG C
~25℃。
Preferably, the Detection wavelength of described ultraviolet spectra detector is 220 ~ 360 nm, preferably 310-320nm.
Preferably, chromatographic column used in the analysis of high performance liquid chromatography enantiomeric excess rate is the hand using glycoprotein as filler
Property post；Mobile phase forms solution by buffer salt solution and organic solvent, and organic solvent is selected from methanol, ethanol, isopropanol and acetonitrile
One or both of, the percentage that organic solvent accounts for mobile phase cumulative volume is more than 0% and less than 5%, preferably greater than 0% and small
In 2%.
In the present invention, (S) -2, the chiral chromatographic analysis condition choosing of 3,4,5- tetra- fluoro- N- (1- hydroxyl -2- bases) benzamides
From following any：
（1）Liquid phase chromatogram condition A：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015mol/L phosphoric acid salt solution
Solution-isopropanol (99:1), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sampling volume 20
μL ；
（2）Liquid phase chromatogram condition B：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015 mol/L phosphate
The aqueous solution-methanol (97:3), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sampling volume 20
μL ；
（3）Liquid phase chromatogram condition C：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015 mol/L phosphate
The aqueous solution-acetonitrile (98:2), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sampling volume 20
μL。
What the present invention obtained has the beneficial effect that：
The present invention uses 2,3,4,5 tetra fluoro benzoic acid acetic anhydride to be performed the derivatization for derivatization reagent and (S) -2- aminopropanols
Reaction, by controlling reaction condition, 2,3,4,5- tetrafluorobenzoic aid acetic anhydrides selectivity and the primary amine in (S) -2- aminopropanols
React, generate (S) -2,3,4,5- tetra- fluoro- N- (1- hydroxyl -2- bases) benzamides.It is fluoro- to establish (S) -2,3,4,5- four
The HPLC analysis methods of the enantiomeric excess rate of N- (1- hydroxyl -2- bases) benzamide, so as to reach analysis (S) -2- aminopropans
The purpose of alcohol.This method is simple to operate, favorable reproducibility, high sensitivity, accuracy are strong, is easy to normalizing operation, derivatization product
Property is stable.
Brief description of the drawings
Fig. 1：(RS) four fluoro- N- of -2,3,4,5- (1- hydroxyl -2- bases) benzamide sample chiral chromatographic analysis figure；
Fig. 2：(S) four fluoro- N- of -2,3,4,5- (1- hydroxyl -2- bases) benzamide sample chiral chromatographic analysis figure；
In the accompanying drawings：1 is (R) -2, and 3,4,5- tetra- fluoro- N- (1- hydroxyl -2- bases) benzamides, 2 be 2,3,4,5- phenyl tetrafluorides
Arboxylic acid acid anhydride, 3 be (S) -2,3,4,5- tetra- fluoro- N- (1- hydroxyl -2- bases) benzamides.
Embodiment
In order to be more clearly understood that the technology contents of the present invention, described in detail especially exemplified by following examples.
Embodiment 1：(RS) the chiral purity analysis of -2- aminopropanols
Precision weighs (RS) -2- aminopropanols about 25mg and put in 25ml measuring bottles, adds about 0.2ml derivative reagent（Derivative reagent：
18g tetrafluorobenzoic aid acetic anhydrides, the dilution of 200ml absolute methanols）, add mobile phase to be diluted to scale, shake up, take 0.5ml to add flowing
Phase dilution is to 10ml, as test solution.
（1）Liquid phase chromatogram condition A：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015mol/L phosphoric acid
Saline solution-isopropanol (99:1), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sample introduction body
20 μ L of product.Retention time see the table below 1 with separating degree and chiral purity, and its collection of illustrative plates is shown in Fig. 1.
（2）Liquid phase chromatogram condition B：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015 mol/L phosphorus
Acid salt aqueous solution-methanol (97:3), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sample introduction body
20 μ L of product.Retention time see the table below 1 with separating degree and chiral purity.
（3）Liquid phase chromatogram condition C：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015 mol/L phosphorus
Acid salt aqueous solution-acetonitrile (98:2), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sample introduction body
20 μ L of product.Retention time see the table below 1 with separating degree and chiral purity.
The chiral purity analysis of table 1 (RS)-tetrafluoro benzoyl -2- aminopropanols
Embodiment 2：(S) the chiral purity analysis of -2- aminopropanols
Precision weighs (S) -2- aminopropanols about 25mg and put in 25ml measuring bottles, adds about 0.2ml derivative reagent（Derivative reagent：
18g tetrafluorobenzoic aid acetic anhydrides, the dilution of 200ml absolute methanols）, add mobile phase to be diluted to scale, shake up, take 0.5ml to add flowing
Phase dilution is to 10ml, as test solution.
（1）Liquid phase chromatogram condition A：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015mol/L phosphoric acid
Saline solution-isopropanol (99:1), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sample introduction body
20 μ L of product.Retention time see the table below 2 with separating degree and chiral purity, and its collection of illustrative plates is shown in Fig. 2.
（2）Liquid phase chromatogram condition B：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015 mol/L phosphorus
Acid salt aqueous solution-methanol (97:3), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sample introduction body
20 μ L of product.Retention time see the table below 2 with separating degree and chiral purity.
（3）Liquid phase chromatogram condition C：ChromTech CHIRAL-AGP chromatographic columns, mobile phase are 0.015 mol/L phosphorus
Acid salt aqueous solution-acetonitrile (98:2), ultraviolet detection wavelength is 320nm, and flow velocity is 0.8 mL/min, and column temperature is 30 DEG C, sample introduction body
20 μ L of product.Retention time see the table below 2 with separating degree and chiral purity.
The chiral purity analysis of table 2 (RS)-tetrafluoro benzoyl -2- aminopropanols
In this description, the present invention is described with reference to its specific embodiment.But it is clear that it can still make various
Modification and conversion are without departing from the spirit and scope of the present invention.Therefore, specification and drawings be considered as it is illustrative rather than
Restricted.
Claims (6)
1. the HPLC detection methods of one kind (S) -2- aminopropanol chiral purities, it is characterised in that comprise the steps of：
Step 1, derivatization
By (S) -2- aminopropanols (III), at ambient temperature, with 2,3,4,5- tetrafluorobenzoic aid acetic anhydrides (II) for derivatization
Reagent, regulation (S) -2- aminopropanols (III) and 2, the mol ratio of 3,4,5- tetrafluorobenzoic aid acetic anhydrides (II), is performed the derivatization
Reaction generation (S) -2,3,4,5- four fluoro- N- (1- hydroxyl -2- bases) benzamide (I)；
Step 2, HPLC analyses
Using RPLC-ultraviolet spectra detector to four fluoro- N- of (S) -2,3,4,5- (1- hydroxyl -2- bases) benzene
Formamide (I) carries out enantiomeric excess rate analysis, and then obtains to (S) -2- aminopropanols (III) enantiomeric excess rate data；
。
2. the HPLC analysis methods of one kind (S) -2- aminopropanols according to claim 1, it is characterised in that dilution derives
The organic solvent of reagent is selected from combination more than one or both of methanol, toluene, dichloromethane.
3. the HPLC analysis methods of one kind (S) -2- aminopropanols according to claim 1, it is characterised in that (S) -
The mol ratio of 2- aminopropanols and 2,3,4,5 tetra fluoro benzoic acid acetic anhydride is 1:0.5~1:1.
4. the HPLC analysis methods of one kind (S) -2- aminopropanols according to claim 1, it is characterised in that the room
It is 10 DEG C ~ 30 DEG C to refer to range of reaction temperature under the conditions of temperature；Preferably temperature range is 20 DEG C ~ 25 DEG C.
5. the HPLC analysis methods of one kind (S) -2- aminopropanols according to claim 1, it is characterised in that described
The Detection wavelength of ultraviolet spectra detector is 220 ~ 360 nm, preferably 310-320nm.
6. the HPLC analysis methods of one kind (S) -2- aminopropanols according to claim 1, it is characterised in that efficient liquid
Chromatographic column used in the analysis of phase chromatogram enantiomeric excess rate is the chiral column using glycoprotein as filler；Mobile phase is molten by buffer salt
Liquid and organic solvent composition solution, organic solvent are selected from one or both of methanol, ethanol, isopropanol and acetonitrile, You Jirong
The percentage that agent accounts for mobile phase cumulative volume is more than 0% and less than 5%, preferably greater than 0% and less than 2%.
Priority Applications (1)
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| CN201610620357.9A CN107677735A (en) | 2016-08-02 | 2016-08-02 | A kind of HPLC analysis methods of (S) 2 aminopropanol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109781891A (en) * | 2019-02-16 | 2019-05-21 | 安徽诺全药业有限公司 | A kind of liquid phase detection method of chirality 2- amino n-butanol |
| CN114624351A (en) * | 2020-12-14 | 2022-06-14 | 宜昌人福药业有限责任公司 | Analysis method for (R) - (-) -1-amino-2-propanol residue in benzene sulfonic acid remazolam bulk drug |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109781891A (en) * | 2019-02-16 | 2019-05-21 | 安徽诺全药业有限公司 | A kind of liquid phase detection method of chirality 2- amino n-butanol |
| CN114624351A (en) * | 2020-12-14 | 2022-06-14 | 宜昌人福药业有限责任公司 | Analysis method for (R) - (-) -1-amino-2-propanol residue in benzene sulfonic acid remazolam bulk drug |
| CN114624351B (en) * | 2020-12-14 | 2024-04-09 | 宜昌人福药业有限责任公司 | Analysis method of (R) - (-) -1-amino-2-propanol residues in pomazolam besylate bulk drug |
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