Several methods have been developed to prepare 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 2 with good to high enantiomeric excess: 70 and 93% ees have in fact been obtained by baker's yeast-induced asymmetric reduction of the ketone precursor 1 and by kinetic resolution performed in the presence of lipase from Pseudomonas sp. (E = 38), respectively. Compounds (R)-(+)-2 and (S)-(-)-2 have also been prepared by a chemical method in 90% yield and with enantiomeric excesses of 98 and 96.4%, respectively. HPLC on Chiralcel OD column separation of enantiomers (separability factor alpha = 1.64) has also been successfully performed. Compound 2 could, in turn, be used for the synthesis in an optically active form of various molecules, including beta-aminoalcohols 6, drugs with potential beta-blocker activity.

Chemical and Chemoenzymatic Routes to 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol, a precursor of drugs with potential ƒÒ-blocker activity

FRANCHINI, Carlo;SCILIMATI, Antonio;TORTORELLA, Paolo
2000-01-01

Abstract

Several methods have been developed to prepare 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 2 with good to high enantiomeric excess: 70 and 93% ees have in fact been obtained by baker's yeast-induced asymmetric reduction of the ketone precursor 1 and by kinetic resolution performed in the presence of lipase from Pseudomonas sp. (E = 38), respectively. Compounds (R)-(+)-2 and (S)-(-)-2 have also been prepared by a chemical method in 90% yield and with enantiomeric excesses of 98 and 96.4%, respectively. HPLC on Chiralcel OD column separation of enantiomers (separability factor alpha = 1.64) has also been successfully performed. Compound 2 could, in turn, be used for the synthesis in an optically active form of various molecules, including beta-aminoalcohols 6, drugs with potential beta-blocker activity.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/129871
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