Unlock instant, AI-driven research and patent intelligence for your innovation.
Preparation method of high-purity chiral sulphoxide compound
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A compound and sulfoxide technology, which is applied in the field of preparation of high-purity chiral sulfoxide compounds, can solve the problems such as few reports of biocatalysis methods, and achieves the advantages of being beneficial to large-scale production, simple and feasible preparation methods, and utilization of raw materials. high effect
Active Publication Date: 2011-11-16
苏州特瑞药业股份有限公司
View PDF1 Cites 10 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
Chiral sulfoxide compounds can be prepared by four chemical and biocatalytic methods: chiral resolution, chiral-assisted induction, chiral reagent conversion, and asymmetric catalytic synthesis. Biocatalytic methods are rarely reported.
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0036] Synthesis of chiral catalyst titanium complex:
[0037] Add 8g of titanium isopropoxide, 8.8g of aminoindanol, and 125ml of toluene to a 500ml three-neck flask in turn, start stirring, add 0.2ml of pure water after 5 minutes, then raise the temperature to 54°C, keep warm for 1h, the reaction is completed, and directly used for next step of synthesis.
Embodiment 2
[0039] The synthesis of L-rabeprazole, the reaction formula is as follows:
[0040]
[0041] Add 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfur]- 1 Hydrogen-benzimidazole (rabeprazolesulfide) 32g, heat up to 50°C, keep warm for 30min, observe whether the raw material is completely dissolved, if not clear, then slowly raise the temperature by 5°C. After the reaction system is clarified, start to cool down to 10°C, add 3.6g of N,N-diisopropylethylamine, continue to cool down to -5-0°C, add 11.8g of tert-butyl hydroperoxide dropwise (the control time is 1h to complete the addition) , temperature 0-5°C), add 5-15°C and keep warm for 2 hours, take a sample to check whether the reaction is complete (if not, continue to keep warm until the raw material is completely converted). After the reaction, add 100ml of 12% ammonia water and stir for 1 hour, then remove the oil layer, extract the oil layer with 50ml of 12% ammonia water and merge it into the water layer, after...
Embodiment 3
[0043] The synthesis of L-pantoprazole, reaction formula is as follows:
[0044]
[0045] Add 5-(difluoromethoxy)-2-{[(3,4-dimethoxy-2-pyridyl)methyl]sulfur to the solution of the titanium complex catalyst prepared in Example 1 above -1H-benzimidazole (pantoprazole sulfide) 34.5g, heat up to 50°C, keep warm for 30min, observe whether the raw material is completely dissolved, if not clear, then slowly raise the temperature by 5°C. After the reaction system is clarified, start to cool down to 10°C, add 3.6g of N,N-diisopropylethylamine, continue to cool down to -5-0°C, add 20g of cumene hydroperoxide dropwise (the control time is 1h to complete the addition, Temperature 0-5°C), after adding 5-15°C, keep warm for 2 hours, take a sample to check whether the reaction is complete (if not, continue to keep warm until the raw material is completely converted). After the reaction, add 100ml of 12% ammonia water and stir for 1 hour, then remove the oil layer, extract the oil layer w...
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
Abstract
The invention discloses a preparation method of a high-purity chiral sulphoxide compound, which has high raw material utilization ratio and a simple process. The method comprises the following steps of: adding an alkoxytitanium compound and chiral ligand amino indanol into an organic low-polarity or nonpolar solvent, wherein the molar ratio of the alkoxytitanium compound to the chiral ligand amino indanol is 1:(1.5-3); adding pure water; stirring at the temperature of 25-100 DEG C for 1-2 hours to obtain a chiral catalyst titanium complex; adding thioether corresponding to the chiral sulphoxide compound into a solution of the obtained chiral catalyst titanium complex, wherein the molar ratio of the thioether to the chiral catalyst titanium complex is 1:(0.1-1); adding amine, wherein the molar ratio of thioether to amine is 1:(0.1-0.5); stirring, controlling the temperature between 10 DEG C below zero and 50 DEG C and dropwise adding an oxidant; raising the temperature to 30 DEG C and preserving heat to react for 2 hours till thioether serving as a raw material is fully reacted to obtain a crude chiral sulphoxide compound; and purifying the crude chiral sulphoxide compound to obtain the high-purity chiral sulphoxide compound.
Description
technical field [0001] The invention relates to a chiral sulfoxide compound, in particular to a preparation method of a high-purity chiral sulfoxide compound. Background technique [0002] Chiral sulfoxide compounds have many uses, one of which is as chiral drugs: proton pump inhibitors, such as L-rabeprazole (S-rabepraole), L-pantoprazole (S-pantoprazole), L- Omeprazole (Esomeprazole, also known as esomeprazole), levolansoprazole (S-lansoprazole) and their acceptable basic salts in the pharmaceutical field, namely esomeprazolemagnesium salt, sodium salt, Potassium salt, etc. Chiral sulfoxide compounds can be prepared by four chemical methods and biocatalytic methods, including chiral resolution, chiral-assisted induction, chiral reagent conversion and asymmetric catalytic synthesis. Biocatalytic methods are rarely reported so far. Chiral resolution, chiral-assisted induction, and chiral reagent transformation are all currently used in industry, but from the perspective o...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More