Continuous Separation of Racemic 3,5-Dinitrobenzoyl-Amino Acids in a Centrifugal Contact Separator with the Aid of Cinchona-Based Chiral Host Compounds

摘要

The resolution of racemates is mostly performed by crystallisation of diastereomeric salts. Direct physical separation could be much more efficient, but so far most concepts, with the exception of SMB, have proven to be non-scaleable. Here we report the first scalable process for the resolution of N-protected amino acid derivatives through selective extraction, with the aid of a catalytic amount of a chiral host compound based on Cinchona alkaloids. The method hinges on the use of centrifugal contact separators (CCSs) for fast mixing and separation. Although the highest ee obtained was only 80%, the concept can be extended through the use of a series of CCSs in countercurrent mode to effect full separation.