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Preparative resolution of the enantiomers of Tert ‐leucine derivatives by simulated moving bed chromatography
Author(s) -
Francotte Eric,
Leutert Thomas,
La Vecchia Luiggi,
Ossola Flavio,
Richert Paul,
Schmidt Alfred
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10042
Subject(s) - chemistry , enantiomer , chromatography , heptane , leucine , yield (engineering) , phase (matter) , trifluoroacetic acid , chiral column chromatography , resolution (logic) , cellulose , chiral derivatizing agent , organic chemistry , amino acid , biochemistry , materials science , artificial intelligence , computer science , metallurgy
The enantiomers of two different derivatives of tert ‐leucine were separated by continuous chromatography on chiral stationary phases applying the simulated moving bed technique. About 1 kg of racemic N ‐carbobenzoxy‐ tert ‐leucine was resolved on the cellulose‐based phase Chiralcel OD using a mixture of heptane/ethanol and 0.1% of trifluoroacetic acid modifier as the mobile phase, while 520 g of the N‐Boc‐ tert ‐leucine‐benzylester was resolved on the amylose‐based phase Chiralpak AD with a mixture of heptane/2‐propanol as the mobile phase. In both instances the corresponding enantiomers were obtained in high yield and high optical purity. Chirality 14:313–317, 2002. © 2002 Wiley‐Liss, Inc.