Strained Heterocyclic Compounds. 10. Introduction of an Amide Side Chain in Place of Halogen in 7-Halo-8-oxo-1-azabicyclo[4.2.0]octane.
- 1 January 1976
- journal article
- research article
- Published by Danish Chemical Society in Acta Chemica Scandinavica
- Vol. 30b (4) , 318-322
- https://doi.org/10.3891/acta.chem.scand.30b-0318
Abstract
The nucleophilic displacement reaction between Tl(I) phthalimide and bromo-.beta.-lactams was studied. The corresponding phthalimido-.beta.-lactams were obtained in good yields with 90% stereoselectivity (inversion at the C-7 carbon atom). A chloro-.beta.-lactam reacted only in very low yield under the same conditions. Hydrazinolysis of the phthalimido-.beta.-lactam and subsequent acylation gave a .beta.-lactam with an amido side chain, appropriate for a penicillin analogue.This publication has 0 references indexed in Scilit: