225918-60-5Relevant articles and documents
Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel
Ferraboschi, Patrizia,Mieri, Maria De,Galimberti, Fiorella
scheme or table, p. 2136 - 2141 (2010/10/03)
The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation.
Chemo-enzymatic dynamic kinetic resolution of amino acid thioesters
Arosio, Dario,Caligiuri, Antonio,D'Arrigo, Paola,Pedrocchi-Fantoni, Giuseppe,Rossi, Cristina,Saraceno, Caterina,Servi, Stefano,Tessaro, Davide
, p. 1345 - 1348 (2008/09/16)
The L-forms of racemic-N-protected-β,γa,aunsaturated a-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracemisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities were achieved.