2,2,2-Trifluoroethanol → Dexlansoprazole
Reaction equation
CS([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S@:12]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)=[O:13])[C:6]=1[CH3:23])(=O)=O.[CH2:24]([OH:29])[C:25]([F:28])([F:27])[F:26]>>[CH3:23][C:6]1[C:7]([CH2:11][S@:12]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)=[O:13])=[N:8][CH:9]=[CH:10][C:5]=1[O:29][CH2:24][C:25]([F:28])([F:27])[F:26]Participants
Procedure
In accordance with yet another embodiment of the present invention, there is provided a process for producing (R)-(+)2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzimidazole comprising reacting 4-chloro-2,3-dimethyl-pyridine-1-oxide with sodium methane thiolate to give 2,3-dimethyl-4-methylsulfanyl-pyridine-1-oxide followed by oxidation using a suitable oxidizing agent to obtain (4-methanesulfonyl-2,3-dimethyl-pyridine)-1-oxide, chlorinating the resultant in the presence of suitable chlorinating agent to obtain 2-chloromethyl-4-methanesulfonyl-3-methylpyridine, condensing the 2-chloromethyl-4-methanesulfonyl-3-methylpyridine in presence of a suitable base in a solvent, optionally in the presence of a phase transfer catalyst with 2-mercaptobenzimidazole to obtain 2-(4-methanesulfonyl-3-methyl-pyridine-2-ylmethylsulfonyl)-1-H-benzimidazole, stereoselective oxidation of the 2-(4-methanesulfonyl-3-methyl-pyridine-2-ylmethylsulfonyl)-1-H-benzimidazole using an optically active compound in presence of a metal catalyst and a suitable solvent to obtain (R)-2-(4-methanesulfonyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzimidazole and subsequently reacting the (R)-2-(4-methanesulfonyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzimidazole with trifluoroethanol to obtain the (R)-(+)2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzimidazole.
Sources & evidence
- ORD record
- ord-0970a172f6b64693ba397db13ded1ffc
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513427B2
Reaction notes
Loading…