Conversion process for 2,3-benzodiazepine enantiomers
AssigneeVela Acquisition Corporation
InventorsYong Victoria Wei, Naidaong Ye, Kimm Galbraith, Jianfeng Shi, Wuyi Wang, Yungen Xu, Mallikarjun Reddy Ravi
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Abstract
Methods for the racemization of an enantiomer of a 2,3-benzodiazepine molecule into the corresponding racemic mixture under either basic or acidic conditions are described. Furthermore, the invention relates to the conversion of an enantiomer of tofisopam or its metabolites to the corresponding opposite enantiomer.
Claims18
A method for racemizing an enantiomer of tofisopam to its racemate, the method comprising (a) reacting the enantiomer with one or greater base equivalent of an organic base at a temperature below 20° C. and (b) quenching the reaction with a proton source, thereby obtaining the racemate from the enantiomer.
A method for increasing the yield of a desired enantiomer of tofisopam over an undesired, the method comprising (a) obtaining the undesired enantiomer, (b) reacting the undesired enantiomer with one or greater base equivalent of an organic base at a temperature below 20° C., (c) quenching the reaction with a proton source thereby obtaining a racemate from the undesired enantiomer, and (d) isolating the desired enantiomer from the racemate of step (c).
A method for racemizing an enantiomer of tofisopam to its racemate, the method comprising (a) reacting the enantiomer with an organic or inorganic acid at an elevated temperature in a high temperature boiling organic solvent selected from the group consisting of dimethylsulfoxide, toluene and dioxane and (b) obtaining the racemate from the enantiomer.
A method for increasing the yield of a desired enantiomer of tofisopam from a racemic mixture, the method comprising (a) obtaining the undesired enantiomer, (b) reacting the undesired enantiomer with an organic acid at an elevated temperature in a high temperature boiling organic solvent selected from the group consisting of dimethylsulfoxide, toluene and dioxane, thereby obtaining a racemate from the undesired enantiomer, and (c) isolating the desired enantiomer from the racemate of step (b).
Dependencies are inferred from the claim text.