Invention Grant
- Patent Title: Stereoselective synthesis of benzimidazole sulfoxides
- Patent Title (中): 苯并咪唑亚砜的立体选择性合成
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Application No.: US11865295Application Date: 2007-10-01
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Publication No.: US07928241B2Publication Date: 2011-04-19
- Inventor: Bandi Parthasaradhi Reddy , Kura Rathnakar Reddy , Rapolu Raji Reddy , Dasari Muralidhara Reddy
- Applicant: Bandi Parthasaradhi Reddy , Kura Rathnakar Reddy , Rapolu Raji Reddy , Dasari Muralidhara Reddy
- Applicant Address: IN Hyderabad, Andhrapradesh
- Assignee: Hetero Drugs Limited
- Current Assignee: Hetero Drugs Limited
- Current Assignee Address: IN Hyderabad, Andhrapradesh
- Agency: Caesar, Rivise, Bernstein, Cohen & Pokotilow, Ltd.
- Main IPC: C07D401/12
- IPC: C07D401/12 ; C07D401/14 ; C07D413/04

Abstract:
The present invention relates to a process for stereo selective synthesis of substituted sulfoxides either as a single enantiomer or in an enantiomerically enriched form. Thus, 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl) methyl]thio]-1H-benzimidazole is reacted with (R)-camphorsulfonyl chloride to form a mixture of 1-(R)-camphorsulfonyl-5- (and 6-)methoxy-2-[(3,5-dimethyl-4-methoxy -2-pyridyl)methylthio]-1H-benzimidazole, oxidized to obtain a diastereomeric excess of 1-(R)-camphorsulfonyl-(5- and 6-)-methoxy-2-[(3,5-dimethyl -4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole over 1-(R)-camphorsulfonyl -(5- and 6-)-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl) methyl-(R)-sulfinyl]-1H-benzimidazole, the diastereomers are separated by fractional crystallization and the separated 1-(R)-camphorsulfonyl-(5- and 6-)-methoxy -2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole is deprotected to give esomeprazole.
Public/Granted literature
- US20080076929A1 NOVEL STEREOSELECTIVE SYNTHESIS OF BENZIMIDAZOLE SULFOXIDES Public/Granted day:2008-03-27
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