CN105699509B - A kind of method for separating and detecting of 3- amino butanols enantiomter - Google Patents
A kind of method for separating and detecting of 3- amino butanols enantiomter Download PDFInfo
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Abstract
The invention belongs to Pharmaceutical Analysis technical fields, and in particular to a kind of 3 amino butanol corresponds to the method for separating and detecting of isomers.The present invention provides the method for separating and detecting that a kind of 3 amino butanol corresponds to isomers, with (R) (+) 1 phenylethanesulfonyl chloride is that derivatization reagent and 3 amino butanols carry out quickly double derivative reactions, pass through high performance liquid chromatography and carries out qualitative and quantitative analysis and enantiomeric excess rate measurement with ultraviolet combination.This method derivatization reaction mild condition, quickly, detection sensitivity is high, it is reproducible, be easy to normalizing operation.It can be used for the separation detection to 3 amino butanols and quality control in industrialized production.
Description
Technical field
The invention belongs to Pharmaceutical Analysis technical fields, and in particular to a kind of separation detection of 3- amino butanols enantiomter
Method.
Background technology
(R) -3- amino butanols be synthesize Du Lutewei important intermediate.Du Lutewei is Britain pharmacy giant Ge Lansu
SmithKline（GSK）Under anti-AIDS（HIV）New drug, 2013 Nian8Yue12 food and drug administrations（FDA）.It is preclinical
Result of study display degree Lu Tewei has stronger anti-HIV-1 virus activity, and safety and tolerance are good.
There are two chiral centre in Du Lutewei molecular structures, by chiral source (R) introducing of -3- amino butanols, Du Lutewei
The relative amount of two diastereoisomers is solely dependent upon the relative energy height for generating their transition states, due to generating（4R,
12aS) transition state energy compared with（4R, 12aR) isomers is low, therefore reaction ultimately produced with（4R, 12aS) production based on configuration
Object.Low optical it is pure (R) another isomers in -3- amino butanols, four chipal compounds can be generated in the reaction, reduced
The chiral purity of Du Lutewei, therefore (R) -3- amino butanols optical purity directly determine the optical purity of Du Lutewei,
Impurity is how many and anti-AIDS acts on.Although this new drug Time To Market is very short, since its efficient anti-AIDS effect is drawn
Sent out the wilderness demand to this new drug, so as to cause to Du Lutewei chiral sources (R) -3- amino butanols wilderness demand.Cause
This prepare high standard, high-optical-purity (R) -3- amino butanols, it is of great significance for synthesis new drug Du Lutewei.
Wu Shengwen etc.（CN201410488279.2）N-Cbc- is generated using Carbobenzoxy Chloride and 3- amino butanol derivatizations
3- amino butanols carry out liquid phase detection at 210 nm.Chromatographic column AD-H；Mobile phase n-hexane：Isopropanol（9:1）；Retention time
S- isomers 11.1 minutes, R- isomers 12.2 minutes, detection have used expensive normal phase column.R. H. BUCK etc.
（Journal of chromatography）3- amino butanols are performed the derivatization with o-phthalaldehyde-thiol derivatives, color
Spectral condition：Knauer Hypersil ODS pillars, 0.05% sodium phosphate buffer salting liquid of mobile phase/methanol（Volume ratio 35/
65）, pH 7.0, fluoroscopic examination.
3- amino butanols compound contains a primary amine and a hydroxyl without UV absorption, molecular structure, establish efficiently, it is accurate
Really reliable optical purity analysis method difficulty is very big.It is quickly double derivative by being carried out with the chiral reagent with UV absorption
Change, obtain existing UV absorption again there are three chiral radicals derivative, can be directly in RP-HPLC and ultraviolet combination
The upper analysis for carrying out isomers.
Invention content
It is an object of the invention to overcome the deficiencies of existing technologies, a kind of separation of 3- amino butanols enantiomter is provided
Detection method fast can accurately realize qualitative, quantitative and enantiomeric excess rate analysis.
To achieve the goals above, the technical solution adopted by the present invention is as follows：
A kind of method for separating and detecting of 3- amino butanols enantiomter, specifically comprises the following steps：
Step 1: derivatization
3- amino butanols are dissolved in organic solvent, in a certain temperature conditions, with (R)-(+) -1- phenyl second sulphonyl
Chlorine is derivatization reagent, control 3- amino butanols and (R)-(+) -1- phenylethanesulfonyl chlorides molar ratio, perform the derivatization reaction,
The 3- amino butanols after derivatization are obtained, reaction equation is shown in Formulas I；
Formulas I
Step 2: separation detection
Using reversed-phase high performance liquid chromatography-UV detector to the 3- amino butanols after derivatization carry out it is qualitative, quantitative and
Enantiomeric excess rate measures.
The organic solvent is selected from petroleum ether, dichloromethane, 1,2- dichloroethanes, tetrahydrofuran, chloroform and four chlorinations
The combination of one or more of carbon.
The volume ratio of the organic solvent and 3- amino butanols is 10 ~ 500:1, preferably 10 ~ 50:1.
The certain temperature refers to from -10 DEG C to reflux temperature, preferably 15 ~ 35 DEG C.
The reflux temperature concrete numerical value of the present invention is related with the selection of organic solvent, and those skilled in the art can be according to molten
The selection of agent clearly determines the range of reflux temperature.
The 3- amino butanols and (R)-(+) -1- phenylethanesulfonyl chlorides molar ratio be 1:2~20.
The Detection wavelength of the UV detector is 210 ~ 300nm, preferably 220 ~ 260nm.
The chromatographic column that the reversed-phase high performance liquid chromatography uses is common reversed-phase column.Preferred chromatographic column is reverse phase C18
Column, most preferably enlightening horse reverse phase C18 columns（250 × 4.6mm, 5 μm, pH ranges 2.0 ~ 8.0）.
The mobile phase of the reversed-phase high performance liquid chromatography is made of water and organic solvent, and organic solvent is selected from methanol, second
One or both of alcohol, isopropanol and acetonitrile；Organic solvent accounts for the volume ratio ranging from 50% ~ 100% of mobile phase, preferably model
Enclose is 60% ~ 80%.
The flow velocity of the mobile phase is 0.2 ~ 3.0mL/min, preferably 1.0mL/min.
In the present invention, rp-hplc analysis condition is preferably：
Enlightening horse reverse phase C18 columns, mobile phase is acetonitrile-water（Volume ratio 80:20）, ultraviolet detection wavelength is 254nm, and flow velocity is
1.0mL/min, column temperature are 30 DEG C, and sample size is 20 μ L.
Compared with prior art, obtained by the present invention to have the beneficial effect that：
The present invention gives the derivatization methods of 3- amino butanols, by control reaction condition, quickly generate (R)-(+)-
The derivative of 1- phenylethanesulfonyl chlorides and 3- amino butanols, and establish to (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations
Qualitative, quantitative and enantiomerism body measurement the HPLC analytical method of 3- amino butanols.This method is easy to operate, again
It is strong to show good property, high sensitivity, accuracy, is convenient for normalizing operation.By to (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations
3- amino butanols carry out the analysis of qualitative, quantitative and enantiomeric excess rate, to realizing to the qualitative, quantitative of 3- amino butanols and
Enantiomeric excess rate（It is chirale.e.Value）Analysis.
Description of the drawings
Fig. 1：(R)-(+) -1- phenylethanesulfonyl chlorides with (R) chromatogram after -3- amino butanol derivatizations；
Fig. 2：(R)-(+) -1- phenylethanesulfonyl chlorides-with (S) chromatogram after -3- amino butanol derivatizations；
Fig. 3：(R)-(+) -1- phenylethanesulfonyl chlorides with (RS) chromatogram after -3- amino butanol derivatizations；
In the accompanying drawings：1 for (R)-(+) -1- phenylethanesulfonyl chlorides with (R) -3- amino butanols derivative；2 for (R)-
(+) -1- phenylethanesulfonyl chlorides and (S) -3- amino butanols derivative.
Specific implementation mode
Further details of narration is carried out to the present invention below in conjunction with attached drawing.
Embodiment 1：(R)-(+) -1- phenylethanesulfonyl chlorides and 3- amino butanol derivatives liquid-phase chromatographic analysis
1-1：(R)-(+) -1- phenylethanesulfonyl chlorides with (R) -3- amino butanol derivatives liquid-phase chromatographic analysis
Take (R) -3- amino butanols 3.09g (0.03mol), it is dissolved in 60mL dichloromethane, stirs, be slowly added at 30 DEG C
(R)-(+) -1- phenylethanesulfonyl chlorides 24.57g (0.12mol).TLC monitoring reactions, be evaporated after reaction (R)-(+)-1-
After phenylethanesulfonyl chloride derivatization (R) -3- amino butanols.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (R) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, retention time and hand
Property purity analysis is shown in Table 1, and collection of illustrative plates is shown in Fig. 1.
1-2：(R)-(+) -1- phenylethanesulfonyl chlorides with (S) -3- amino butanol derivatives liquid-phase chromatographic analysis
Take (S) -3- amino butanols 3.09g (0.03mol), it is dissolved in 40mL chloroforms, stirs, be slowly added at 30 DEG C
(R)-(+) -1- phenylethanesulfonyl chlorides 24.57g (0.12mol).TLC monitoring reactions, be evaporated after reaction (R)-(+)-1-
After phenylethanesulfonyl chloride derivatization (S) -3- amino butanols.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (S) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume.Retention time and hand
Property purity analysis is shown in Table 1, and collection of illustrative plates is shown in Fig. 2.
1-3：(R)-(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanols derivative liquid-phase chromatographic analysis
Weigh (RS) -3- amino butanols 3.09g (0.03mol), it is dissolved in 40mL carbon tetrachloride, is stirred at 30 DEG C, delayed
Be added dropwise slowly (R)-(+) -1- phenylethanesulfonyl chlorides 24.57g (0.12mol).TLC monitoring reactions, be evaporated after reaction (R)-
(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives.
Will (R)-(+) -1- phenylethanesulfonyl chlorides with (RS) after -3- amino butanol derivatives flowing phased soln using efficient
Liquid chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:20）,
Ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume.Retention time and chiral purity
Degree analysis is shown in Table 1, and collection of illustrative plates is shown in Fig. 3.
Table 1 (R)-(+) 3- amino butanols retention time and chirality after -1- phenylethanesulfonyl chloride derivatizationse.e.% values
Embodiment 2：3- amino butanols and (R)-(+) -1- phenylethanesulfonyl chlorides molar ratio investigate experiment
2-1：Weigh (S) -3- amino butanols 3.09g (0.03mol), it is dissolved in 40mL chloroforms, is stirred at 40 DEG C, slowly
Be added (R)-(+) -1- phenylethanesulfonyl chlorides 12.28g (0.06mol).TLC monitoring reactions, be evaporated after reaction (R)-
(+) -1- phenylethanesulfonyl chlorides with (S) -3- amino butanol derivatives.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (S) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, retention time and hand
Propertye.e.% values are the same as embodiment 1-2.
：Weigh (R) -3- amino butanols 3.09g (0.03mol), it is dissolved in 40mL carbon tetrachloride, is stirred at 30 DEG C, delayed
Be added dropwise slowly (R)-(+) -1- phenylethanesulfonyl chlorides 18.43g (0.09mol).TLC monitoring reactions, be evaporated after reaction (R)-
(+) -1- phenylethanesulfonyl chlorides with (R) -3- amino butanol derivatives.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (R) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, retention time and hand
Propertye.e.% values are the same as embodiment 1-1.
：Take (RS) -3- amino butanols 3.09g (0.03mol), it is dissolved in 30mL1, in 2- dichloroethanes, is stirred at 80 DEG C, delayed
Be added slowly (R)-(+) -1- phenylethanesulfonyl chlorides 14.33g (0.07mol).TLC monitoring reactions, be evaporated after reaction (R)-
(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (RS) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, retention time and hand
Propertye.e.% values are the same as embodiment 1-3.
：Weigh (R) -3- amino butanols 3.09g (0.03mol), it is dissolved in 60mL petroleum ethers, stirs, be slowly added at 0 DEG C
(R)-(+) -1- phenylethanesulfonyl chlorides 20.48g (0.1mol).TLC monitoring reactions, be evaporated after reaction (R)-(+) -1- benzene
Base ethyl sulfonic chloride with (R) -3- amino butanol derivatives.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (R) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, retention time and hand
Propertye.e.% values are the same as embodiment 1-1.
：Weigh (S) -3- amino butanols 3.09g (0.03mol), it is dissolved in 500mL（Dichloromethane：Chloroform 1:1）In, 20
It is stirred at DEG C, be slowly added to (R)-(+) -1- phenylethanesulfonyl chlorides 122.85g (0.6mol).TLC monitoring reactions, after reaction
Be evaporated (R)-(+) -1- phenylethanesulfonyl chlorides with (S) -3- amino butanol derivatives.
Will (R)-(+) after -1- phenylethanesulfonyl chloride derivatizations (S) -3- amino butanols with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 80:
20）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, retention time and hand
Propertye.e.% values are the same as embodiment 1-2.
Embodiment 3：Chromatographic condition investigates experiment
（1）Derivatization
Weigh (RS) -3- amino butanols 3.09g (0.03mol), it is dissolved in 60mL dichloromethane, is stirred at 30 DEG C, slowly
Be added dropwise (R)-(+) -1- phenylethanesulfonyl chlorides 24.57g (0.12mol).TLC monitoring reactions, be evaporated after reaction (R)-
(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives.
（2）To (R)-(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives are using following different chromatostrips
Part carries out separation detection
A. incite somebody to action (R)-(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 70:
30）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, chirale.e.% values are same
Embodiment 1-3.
B. incite somebody to action (R)-(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is acetonitrile-water（Volume ratio 90:
10）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, chirale.e.% values are same
Embodiment 1-3.
C. incite somebody to action (R)-(+) -1- phenylethanesulfonyl chlorides-with (RS) -3- amino butanols with flowing phased soln after use efficient liquid
Phase chromatography is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is isopropanol-water（Volume ratio 80:20）,
Ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, chirale.e.% values are the same as implementation
Example 3.
D. incite somebody to action (R)-(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is alcohol-water（Volume ratio 75:
25）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, chirale.e.% values are same
Embodiment 1-3.
E. incite somebody to action (R)-(+) -1- phenylethanesulfonyl chlorides with (RS) -3- amino butanol derivatives with flowing phased soln after using height
Effect liquid phase chromatogram is detected analysis.Liquid phase chromatogram condition：Enlightening horse C18 chromatographic columns, mobile phase is methanol-water（Volume ratio 70:
30）, ultraviolet detection wavelength is 254nm, and flow velocity 1.0mL/min, column temperature is 30 DEG C, 20 μ L of sampling volume, chirale.e.% values are same
Embodiment 1-3.
Embodiment described above is merely a preferred embodiment of the present invention, and the simultaneously exhaustion of the feasible implementation of non-present invention.It is right
For persons skilled in the art, any aobvious to made by it under the premise of without departing substantially from the principle of the invention and spirit and
The change being clear to should be all contemplated as falling within the claims of the present invention.
Claims (8)
1. a kind of method for separating and detecting of 3- amino butanols enantiomter, which is characterized in that specifically comprise the following steps：
Step 1: derivatization
3- amino butanols are dissolved in organic solvent, in a certain temperature conditions, are with (R)-(+) -1- phenylethanesulfonyl chlorides
Derivatization reagent controls the molar ratio of 3- amino butanols and (R)-(+) -1- phenylethanesulfonyl chlorides, performs the derivatization reaction, obtain
3- amino butanols after derivatization, reaction equation are shown in Formulas I；
Formulas I
Step 2: separation detection
Qualitative, quantitative and mapping is carried out to the 3- amino butanols after derivatization using reversed-phase high performance liquid chromatography-UV detector
Body overrate measures；
Organic solvent described in step 1 is selected from petroleum ether, dichloromethane, 1,2- dichloroethanes, tetrahydrofuran, chloroform and four
The combination of one or more of chlorination carbon；
The molar ratio of the 3- amino butanols and (R)-(+) -1- phenylethanesulfonyl chlorides is 1:2~20；
Certain temperature refers to 15 ~ 35 DEG C；
The chromatographic column that the reversed-phase high performance liquid chromatography uses is reverse phase C18 columns, and mobile phase is made of water and organic solvent, organic
Solvent is selected from one or both of methanol, ethyl alcohol, isopropanol and acetonitrile；Organic solvent accounts for the volume ratio of mobile phase ranging from
50%~100%。
2. a kind of method for separating and detecting of 3- amino butanols enantiomter according to claim 1, which is characterized in that step
The volume ratio of organic solvent and 3- amino butanols described in rapid one is 10 ~ 500:1.
3. a kind of method for separating and detecting of 3- amino butanols enantiomter according to claim 1, which is characterized in that step
The volume ratio of organic solvent and 3- amino butanols described in rapid one is 10 ~ 50:1.
4. a kind of method for separating and detecting of 3- amino butanols enantiomter according to claim 1, which is characterized in that institute
The Detection wavelength for the UV detector stated is 210 ~ 300nm.
5. a kind of method for separating and detecting of 3- amino butanols enantiomter according to claim 1, which is characterized in that institute
The Detection wavelength for the UV detector stated is 220 ~ 260nm.
6. a kind of method for separating and detecting of 3- amino butanols enantiomter according to claim 1, which is characterized in that institute
The flow velocity for the mobile phase stated is 0.2 ~ 3.0mL/min.
7. a kind of method for separating and detecting of 3- amino butanols enantiomter according to claim 1, which is characterized in that institute
The flow velocity for the mobile phase stated is 1.0mL/min.
8. special according to a kind of method for separating and detecting of 3- amino butanols enantiomter of claim 1-7 any one of them
Sign is that the analysis condition of the reversed-phase high performance liquid chromatography is：
Enlightening horse reverse phase C18 columns, mobile phase is that volume ratio is 80:20 acetonitrile-water, ultraviolet detection wavelength are 254nm, and flow velocity is
1.0mL/min, column temperature are 30 DEG C, and sample size is 20 μ L.
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| 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 |
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