Novel method for preparing chiral sulphoxide compound

A technology for compounds and titanium compounds, applied in the field of chiral sulfoxide compounds, can solve the problems of no enantioselective oxidation of thioethers, no disclosure of a single enantiomer, etc., and achieve the effects of simple method and high optical purity of products
CN101538264AInactive Publication Date: 2009-09-23CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI +1
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
Publication Date
2009-09-23
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention provides a novel method for preparing optically pure substituted [(pyridyl methylene) sulfinyl]-1H-benzimidazole sulphoxide compound by enantioselective synthesis. The method requiring protection is to directly and asymmetrically oxidize prochiral thioether into a corresponding optically pure sulphoxide compound or a sulphoxide compound rich in single enantiomer by a mild and cheap oxidizing agent in the presence of a complex compound catalyst formed by an accessible and stable (+)- or (-)- tartaric acid diamide ligand shown in a general formula and titanium. Therefore, optically pure omeprazole, lansoprazole and pantoprazole can be obtained, wherein R8, R9, R10 and R11 are the same or different, and are selected from hydrogen, alkyl, aralkyl, aryl, organic polymers or a silica loading body.
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Description

field of invention

[0001] The invention relates to a method for preparing enantiomer-enriched or optically pure chiral sulfoxide compounds with anti-peptic ulcer activity by enantioselective catalytic oxidation. technical background

[0002] With 2-[[(2-pyridyl)methylene]sulfinyl]-1H-benzimidazole structure or structurally related sulfoxide compounds I can inhibit H + , K + - The activity of ATPase (also known as proton pump), which inhibits gastric acid secretion, has been widely used to treat peptic ulcers caused by hypersecretion of gastric acid, and its related diseases.

[0003]

[0004] Omeprazole: R 1 =CH 3 , R 2 =OCH 3 , R 3 =CH 3 , R 4 = R 6 = R 7 = H, R 5 =OCH 3

[0005] Lansoprazole: R 1 = H, R 2 =OCH 2 CF 3 , R 3 =CH 3 , R 4 = R 5 = R 6 = R 7 =H

[0006] Pantoprazole: R 1 = H, R 2 =OCH 3 , R 3 =OCH 3 , R 4 = R 6 = R 7 = H, R 5 =OCHF 2

[0007] In the asymmetrically substituted sulfoxide compounds, the sulfur atom is chiral, a...

Claims

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