http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2338556-T3
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_9b4f16ad70ddfeb0b838c113aaae408a |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D401-12 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D401-12 |
| filingDate | 2004-05-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| grantDate | 2010-05-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0bd9a2d92e28f45cda3678582f9e756f http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_86f298c66882cff926861cd940ead4a4 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_ebcef3dcd6fe056ac61f26c09b81b855 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_1e281536d0b4fc5374dfb2d4e10ab0d3 |
| publicationDate | 2010-05-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | ES-2338556-T3 |
| titleOfInvention | NOVEDOUS STEREOSELECTIVE SYNTHESIS OF SULFOXIDES OF BENZIMIDAZOL. |
| abstract | Stereoselective synthesis to prepare a benzimidazole sulfoxide of formula I or a salt thereof, either as an individual enantiomer or in an enantiomerically enriched form: ** (See formula) ** in which R is ** (See formula) * * X is ** (See formula) ** and R1 - R4 are the same or different and are selected from hydrogen, alkyl, alkoxy, halogen, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, oxazolyl, trifluoroalkyl, or the groups R1 - R4 adjacent form ring structures that can be further substituted; wherein R5 and R7 are the same or different and are selected from hydrogen, alkyl, alkylthio, alkoxy optionally substituted by fluorine, alkoxyalkoxy, dialkylamino, piperidino, morpholino, halogen, phenylalkyl and phenylalkoxy; R6 is selected from hydrogen, alkyl, alkylthio, alkoxy optionally substituted by fluorine, alkoxyalkoxy, dialkylamino, piperidino, morpholino, halogen, nitro, phenylalkyl and phenylalkoxy; R8 is hydrogen or forms an alkylene chain together with R7 and R9 and R10 are the same or different and are selected from hydrogen, halogen and alkyl; comprising: a) reacting a benzimidazole sulfide of formula II, or a salt thereof: ** (See formula) ** in which R, X and R1-R4 are as defined for formula I; with a chiral compound of formula III: ** (See formula) ** in which RC-Z- is (S) or (R) -sulfonyl camphor; and Y is a leaving group to provide a compound of formula IV: ** (See formula) ** in which R, X and R1-R4 are as defined for Formula I; and RC-Z- are as defined for formula III: b) oxidize the compound of formula IV to provide a diastereomeric excess of compound of formula V: ** (See formula) ** in which R, X, R1 - R4 and RC-Z- are as defined for formula IV and the star (*) refers to an excess of one configuration in the sulfur atom of the sulfoxide group in relation to the opposite configuration; c) if required, separate the diastereomers of formula V; and d) unprotect the product from step (b); or the diastereomers separated from step (c) with an acid or a base to provide an individual enantiomer or an enantiomerically enriched compound of formula I and, optionally, convert the enantiomer formed in the salt. |
| priorityDate | 2004-05-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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