Candida antarctica lipase B-catalyzed ring opening of 4-arylalkyl-substituted β-lactams |
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| Institution: | 1. Institute of Pharmaceutical Chemistry, Academy of Sciences, University of Szeged, H-6720 Szeged Eötvös utca 6, Hungary;2. Research Group of Stereochemistry of the Hungarian, Academy of Sciences, University of Szeged, H-6720 Szeged Eötvös utca 6, Hungary |
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| Abstract: | The Lipolase-catalyzed ring opening of racemic 4-benzyl- 3 and 4-phenylethyl-2-azetidinone 4 was performed with 0.5 equiv of H2O in diisopropyl ether at 45 °C. The resulting (S)-β-amino acid 5 or 6 (ee ⩾ 87%) and (R)-β-lactam 7 or 8 (ee >99%) enantiomers could easily be separated. The ring opening of enantiomeric β-lactams with 18% aqueous HCl afforded the corresponding enantiopure β-amino acid hydrochlorides 9 and 10 (ee >99%). |
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