Stereoselective synthesis of benzimidazole sulfoxides

Details Stereoselective synthesis of benzimidazole sulfoxides Stereoselective synthesis of benzimidazole sulfoxides

2011-04-19

2011-04-19

Morris, Patricia L (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S210000, C544S124000

Reexamination Certificate

active

07928241

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.

REFERENCES:
patent: 4738974 (1988-04-01), Brandstrom
patent: 5714504 (1998-02-01), Lindberg
patent: 5877192 (1999-03-01), Lindberg
patent: 5948789 (1999-09-01), Larsson
patent: 6559167 (2003-05-01), Garst
patent: 4035455 (1992-05-01), None
patent: 5129 (1979-10-01), None
patent: 221041 (1987-05-01), None
patent: WO 9427988 (1994-12-01), None
patent: WO 2004002982 (2004-01-01), None
Dorwald , Side Reactions in Organic Synthesis, 2005, Wiley: VCH Weinheim Preface, pp. 1-15 & Chapter 8, pp. 279-308.
Sigrist-Nelson K, Krasso A, Muller RK, Fischli AE. Ro 18-5364, a potent new inhibitor of the gastric (H+ + K+)-ATPase. Eur J Biochem. Jul. 15, 1987;166(2):453-9.
PCT International Search Report Dated May 28, 2004.

Affiliated with

Also associated with

Rating

Stereoselective synthesis of benzimidazole sulfoxides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Stereoselective synthesis of benzimidazole sulfoxides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Stereoselective synthesis of benzimidazole sulfoxides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2697886