CN105510510A - HPLC analytical method for chirality purity of 2-amino butanol - Google Patents
HPLC analytical method for chirality purity of 2-amino butanol Download PDFInfo
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Abstract
The invention belongs to the technical field of pharmaceutical analysis and specifically relates to a HPLC (High Performance Liquid Chromatography) analytical method for chirality purity of 2-amino butanol. The method comprises the following steps: by taking R-alpha-methyl-2-naphthalene acetylchloride as a derivatization reagent, performing quick double-derivatization reaction with 2-amino butanol, generating ultraviolet absorption ramifications, and then determining the nature, quantity and chirality purity of 2-amino butanol by using HPLC and ultraviolet. According to the method, the derivatization reaction is quick and mild in reaction conditions; the detection sensitivity is high; the repeatability is excellent; the method can be used for effectively detecting the chirality purity of 2-amino butanol; the standardizing operation is easily performed; the method has practical application value and practical significance.
Description
Technical field
The invention belongs to Pharmaceutical Analysis technical field, be specifically related to a kind of HPLC analytical approach of 2-amino butanol chiral purity.
Background technology
(R)-2-amino butanol is the important intermediate of synthesis R-lansoprazole.U.S. FDA ratifies esophagitis treatment new drug R-lansoprazole (the general Dexlansoprazole by name) listing of Japanese Takeda Pharmaceutical Company Limited research and development on January 30th, 2009.This medicine is the enantiomorph of proton pump inhibitor Lansoprazole, be otherwise known as Dexlansoprazole, be used for the treatment of relevant heartburn sick to Non-erosive gastroesophageal reflux and erosive esophagitis in various degree, clinically show that this poisonous side effect of medicine is lower and patient tolerability good.
R-lansoprazole has a chiral center, this chiral center is introduced by (R)-2-amino butanol, if (R) optical purity of-2-amino butanol is lower, then can there is another isomeride, the chiral purity of R-lansoprazole will be reduced like this, so the optical purity that the optical purity of (R)-2-amino butanol directly affects R-lansoprazole also just affects the curative effect that R-lansoprazole treats esophagitis.Although this new drug Time To Market is not very long, because its efficient treatment esophagitis effect and hypotoxicity have caused the heavy demand to this new drug, thus cause the heavy demand to R-lansoprazole chiral source (R)-2-amino butanol.Therefore prepare (R)-2-amino butanol of high standard, high-optical-purity, synthesis new drug R-lansoprazole is had important practical significance.
Feng Guichun etc. (CN101024617A), Ye Fei etc. (CN101863779A), Zang Li etc. (Chemical Industry in Guangzhou) carry out the analysis of chiral purity by measuring specific rotation angle value.Measure chiral purity by specific rotation angle value, the error at measurment for high-purity (R)-2-amino butanol is larger.Carry out two derivatization fast with the chiral reagent of band uv absorption, the derivant that existing uv absorption forms again three chiral radicals can be obtained, can detect under UV-detector, directly can be carried out again the separation detection of isomeride by RP-HPLC.
Containing a primary amine and a hydroxyl in 2-amino butanol molecular structure, there is no the functional group of uv absorption, cause setting up convenient, fast, reliable optical purity analysis method difficulty very large.It is high that HPLC detection method has separation efficiency, and selectivity is good, and detection sensitivity is high, operation automation, the advantages such as applied range, is analytical approach conventional in present analysis chemistry.But because 2-amino butanol and chiral isomer thereof almost do not have uv absorption, use conventional UV detect to there is end and absorb the problems such as interference, strengthen so usually adopt derivatization method to make it uv absorption thus improve detection sensitivity.
Summary of the invention
The object of the invention is to the defect overcoming prior art, a kind of HPLC analytical approach of 2-amino butanol chiral purity is provided, fast can realize qualitative, quantitative and the analysis of enantiomeric excess rate accurately.
To achieve these goals, the technical scheme taked of the present invention is as follows:
A HPLC analytical approach for 2-amino butanol chiral purity, specifically comprises following steps:
Step one, derivatization
2-amino butanol is dissolved in organic solvent, under certain temperature conditions, with (R)-alpha-methyl-2-naphthalene acetyl chloride for derivatization reagent, the mol ratio of control 2-amino butanol and (R)-alpha-methyl-2-naphthalene acetyl chloride, carry out derivative reaction, obtain the 2-amino butanol after derivatization, reaction equation is shown in formula I;
Formula I
Step 2, separation detect
Reversed-phase high-performance liquid chromatography-UV-detector is adopted to carry out qualitative, quantitative and enantiomeric excess rate mensuration to the 2-amino butanol after derivatization.
Described organic solvent is selected from one or more the combination in methylene chloride, 1,2-ethylene dichloride, toluene, dimethylbenzene, sherwood oil, tetrahydrofuran, chloroform and phenixin.
The volume ratio of described organic solvent and 2-amino butanol is 0.5 ~ 300:1, preferably 2 ~ 20:1.
Described uniform temperature refers to from 0 DEG C to reflux temperature, is preferably 20 ~ 35 DEG C.
The concrete numerical value of reflux temperature of the present invention is relevant with the selection of organic solvent, and those skilled in the art clearly can determine the scope of reflux temperature according to the selection of solvent.
The mol ratio of described 2-amino butanol and (R)-alpha-methyl-2-naphthalene acetyl chloride is 1:4 ~ 20.
The determined wavelength of described UV-detector is 200 ~ 300nm, preferably 230 ~ 260nm.
The chromatographic column that described reversed-phase high-performance liquid chromatography uses is common reversed-phase column.Preferably, chromatographic column is anti-phase C18 post, and most preferred is the anti-phase C18 post of enlightening horse (250 × 4.6mm, 5 μm, pH scope 2.0 ~ 8.0).
The mobile phase of described reversed-phase high-performance liquid chromatography is made up of aqueous acid and organic solvent, organic solvent be selected from methyl alcohol, ethanol, isopropyl alcohol and acetonitrile one or both; The volume ratio scope that organic solvent accounts for mobile phase is 30% ~ 90%, and preferable range is 60% ~ 80%.
The acid of described mobile phase can be organic acid or mineral acid, is preferably mineral acid, as acetic acid, sulfuric acid, nitric acid, hydrochloric acid, is more preferably hydrochloric acid, most preferably is the hydrochloric acid solution of 0.2 ~ 1mol/L.
The pH value of described buffered saline solution is 2.0 ~ 6.0, and preferable ph is 3.0 ~ 5.0.
Described flow rate of mobile phase is at 0.1 ~ 3.0mL/min, and optimum flow rate is 1.0mL/min.
In the present invention, rp-hplc analysis condition is preferably: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, sampling volume 20 μ L.
Compared with prior art, the beneficial effect acquired by the present invention is as follows:
The present invention gives the derivatization method of 2-amino butanol, by controlling reaction conditions, the derivant of quick generation (R)-alpha-methyl-2-naphthalene acetyl chloride and 2-amino butanol, and the HPLC analytical method establishing the qualitative, quantitative of the 2-amino butanol after to (R)-alpha-methyl-2-naphthalene acetyl chloride derivatization and enantiomerism body measurement.The method is simple to operate, favorable reproducibility, highly sensitive, accuracy are strong, is convenient to normalizing operation.By carrying out qualitative, quantitative and chiral purity analysis to the 2-amino butanol after (R)-alpha-methyl-2-naphthalene acetyl chloride derivatization, thus realize the qualitative, quantitative of 2-amino butanol and chiral purity analysis.
Accompanying drawing explanation
Fig. 1: chromatogram after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivatization;
In the accompanying drawings: 1 is (R)-alpha-methyl-2-naphthalene acetyl chloride and the derivant of (R)-2-amino butanol; 2 is the (derivant of (R)-alpha-methyl-2-naphthalene acetyl chloride-and (S)-2-amino butanol.
Embodiment
Below in conjunction with specific embodiment, detailed further describing is carried out to the present invention.
Embodiment 1:(R) liquid-phase chromatographic analysis of derivant of-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol
Get (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 50mL methylene chloride, stir at 30 DEG C, slowly add (R)-alpha-methyl-2-naphthalene acetyl chloride 19.67g (0.09mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chiral purity analysis in table 1, Fig. 1 is shown in by its collection of illustrative plates.
2-amino butanol retention time after table 1 (R)-alpha-methyl-2-naphthalene acetyl chloride derivatization and chirality e.e.% value
The derivatising condition of embodiment 2:2-amino butanol and (R)-alpha-methyl-2-naphthalene acetyl chloride investigates test
2-1: get (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 30mL1, in 2-ethylene dichloride, stirs at 60 DEG C, slowly adds (R)-alpha-methyl-2-naphthalene acetyl chloride 218.6g (0.1mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chirality e.e.% value are with embodiment 1.
: the liquid-phase chromatographic analysis of (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant
Get (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 40mL chloroform, stir at 40 DEG C, slowly add (R)-alpha-methyl-2-naphthalene acetyl chloride 26.23g (0.12mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chirality e.e.% value are with embodiment 1.
: take (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 40mL phenixin, stir at 30 DEG C, slowly drip (R)-alpha-methyl-2-naphthalene acetyl chloride 32.79g (0.15mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chirality e.e.% value are with embodiment 1.
: take (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 50mL sherwood oil, stir at 0 DEG C, slowly add (R)-alpha-methyl-2-naphthalene acetyl chloride 65.58g (0.3mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chirality e.e.% value are with embodiment 1.
: take (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 80mL tetrahydrofuran, stir at 0 DEG C, slowly drip (R)-alpha-methyl-2-naphthalene acetyl chloride 24.05g (0.11mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chirality e.e.% value are with embodiment 1.
: get (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 80mL(sherwood oil: tetrahydrofuran 1:2) in, stir at 38 DEG C, slowly add (R)-alpha-methyl-2-naphthalene acetyl chloride 13.12g (0.06mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
Adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% methyl alcohol-20% hydrochloric acid solution, and the volumetric molar concentration of described hydrochloric acid solution is 0.2mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, retention time and chirality e.e.% value are with embodiment 1.
Embodiment 3: chromatographic condition investigates test
(1) derivatization
Get (RS)-2-amino butanol 3.09g (0.03mol), be dissolved in 50mL methylene chloride, stir at 30 DEG C, slowly add (R)-alpha-methyl-2-naphthalene acetyl chloride 19.67g (0.09mol).TLC monitors reaction, and reaction terminates rear evaporate to dryness and obtains (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant.
(2) adopt following different chromatographic condition to carry out separation to (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant to detect
A. adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 40% acetonitrile-60% hydrochloric acid solution, and the concentration of described hydrochloric acid solution is 0.3mol/L, and pH value is 3.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, chirality e.e.% value is with embodiment 1.
B. adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase for the concentration of the hydrochloric acid solution described in 80% isopropyl alcohol-20% hydrochloric acid solution be 0.3mol/L, pH value is 3.0.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 25 DEG C, and sampling volume 20 μ L, chirality e.e.% value is with embodiment 1.
C. adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 80% ethanol-20% hydrochloric acid solution, and the concentration of described hydrochloric acid solution is 0.3mol/L, and pH value is 4.5.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 25 DEG C, and sampling volume 20 μ L, chirality e.e.% value is with embodiment 1.
D. adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 30% methyl alcohol-70% hydrochloric acid solution aqueous solution, and the concentration of described hydrochloric acid solution is 0.1mol/L, and pH value is 5.0.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, chirality e.e.% value is with embodiment 1.
E. adopt high performance liquid chromatography to carry out detection after (R)-alpha-methyl-2-naphthalene acetyl chloride and (RS)-2-amino butanol derivant mobile phase being dissolved to analyze.Liquid phase chromatogram condition: enlightening horse C18 chromatographic column, mobile phase is 60% ethanol-40% hydrochloric acid solution, and the concentration of described hydrochloric acid solution is 0.1mol/L, and pH value is 6.0.UV detect wavelength is 254nm, and flow velocity is 1.0mL/min, and column temperature is 30 DEG C, and sampling volume 20 μ L, chirality e.e.% value is with embodiment 1.
The above embodiment is only the preferred embodiments of the present invention, and and the feasible enforcement of non-invention exhaustive.For persons skilled in the art, to any apparent change done by it under the prerequisite not deviating from the principle of the invention and spirit, all should be contemplated as falling with within claims of the present invention.
Claims (10)
1. a HPLC analytical approach for 2-amino butanol chiral purity, is characterized in that, specifically comprise following steps:
Step one, derivatization
2-amino butanol is dissolved in organic solvent, under certain temperature conditions, with (R)-alpha-methyl-2-naphthalene acetyl chloride for derivatization reagent, the mol ratio of control 2-amino butanol and (R)-alpha-methyl-2-naphthalene acetyl chloride, carry out two derivative reaction, obtain the 2-amino butanol after derivatization, reaction equation is shown in formula I;
Formula I
Step 2, separation detect
Reversed-phase high-performance liquid chromatography-UV-detector is adopted to carry out qualitative, quantitative and enantiomeric excess rate mensuration to the 2-amino butanol after derivatization.
2. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, it is characterized in that, described organic solvent is selected from one or more the combination in methylene chloride, 1,2-ethylene dichloride, toluene, dimethylbenzene, sherwood oil, tetrahydrofuran, chloroform and phenixin.
3. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, is characterized in that, the volume ratio of described organic solvent and 2-amino butanol is 0.5 ~ 300:1, preferably 2 ~ 20:1.
4. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, it is characterized in that, described uniform temperature refers to from 0 DEG C to reflux temperature, is preferably 20 ~ 35 DEG C.
5. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, is characterized in that, the mol ratio of described 2-amino butanol and (R)-alpha-methyl-2-naphthalene acetyl chloride is 1:4 ~ 20.
6. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, is characterized in that, the determined wavelength of described UV-detector is 200 ~ 300nm, preferably 230 ~ 260nm.
7. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, is characterized in that, the chromatographic column that described reversed-phase high-performance liquid chromatography uses is common reversed-phase column.
8. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 1, it is characterized in that, the mobile phase of described reversed-phase high-performance liquid chromatography is made up of aqueous acid and organic solvent, organic solvent be selected from methyl alcohol, ethanol, isopropyl alcohol and acetonitrile one or both; The volume ratio scope that organic solvent accounts for mobile phase is 30% ~ 90%, preferably 60% ~ 80%.
9. the HPLC analytical approach of a kind of 2-amino butanol chiral purity according to claim 8, it is characterized in that, the acid of described mobile phase is selected from organic acid or mineral acid; Be preferably mineral acid, comprise acetic acid, sulfuric acid, nitric acid and hydrochloric acid, be more preferably hydrochloric acid.
10. want the HPLC analytical approach of a kind of 2-amino butanol chiral purity described in 8 according to right, it is characterized in that, the pH value of the mobile phase aqueous acid of described reversed-phase high-performance liquid chromatography is 2.0 ~ 6.0, and preferable ph is 3.0 ~ 5.0.
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| CN112964822A (en) * | 2019-12-13 | 2021-06-15 | 武汉武药制药有限公司 | Analysis and separation method of related substance L-2-aminobutyric acid in D-2-aminobutanol |
| CN112964822B (en) * | 2019-12-13 | 2023-10-24 | 武汉武药制药有限公司 | Analysis and separation method of related substance L-2-aminobutyric acid in D-2-aminobutyric acid |
| CN113671077A (en) * | 2021-08-17 | 2021-11-19 | 成都倍特药业股份有限公司 | Detection method of acryloyl chloride and related substances thereof |
| CN113671077B (en) * | 2021-08-17 | 2023-08-18 | 成都倍特药业股份有限公司 | Method for detecting acryloyl chloride and related substances |
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