Promoted by Samarium Reaction of (3r,4r)-3-((1r)-1-{[Tert-Butyl(dimethyl)Silyl]oxy}Ethyl)-4-Acetoxy-Azetidin-2-one with Methyl 2-Bromopropianate. Unusual Decyclization of Azetidin-2-one Derivative in Approaches to Carbapenems Analogues

Zuleykha R Valiullina, Lidiya S Khasanova, Natalia K Selezneva, Yu N Belokon, Leonid V Spirikhin and Mansur S Miftakhov
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Yu N Belokon: Ufa Institute of Chemistry of the Russian Academy of Sciences, Russia
Mansur S Miftakhov: AN Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Russia

Organic & Medicinal Chemistry International Journal, 2017, vol. 2, issue 5, 108-112

Abstract: The reaction of the title compound 1 with Sm-reagent prepared from powdered Sm, catalytic amounts of I2 and methyl 2-bromopropionate in THF, leads to the anomalous substituted product 3. The alkylation of the last compound with methyl bromoacetate gives methyl 2-[(2S,3S)-3-((1R)-1-{[tert-butyl(dimethyl) silyl]oxy}ethyl)-1-(2-methoxy-2-oxoethyl)-4-oxoazetidine-2-yl]-2-methyl-3-oxopentanoate 5 which under the action of NaHMDS in THF at -78° undergoes fragmentation with a disconnection of N1-C4-bond and the formation of acyclic amide 7. Possible stepwise formation routes of 3 and 7 are discussed.

Keywords: juniper publishers:Medicinal Chemistry; Biochemistry Journal; Pharmacology Journal; biochemical pharmacology; molecular pharmacology; biochemistry; open access journals; peer reviewed journals; Open Access; Journal of Molecular Biochemistry; International Research Journal of Pure and Applied Chemistry; World Journal of Biological Chemistry; Biochemistry and Analytical Biochemistry; Biochemistry & Physiology: Open Access; Molecular Biology International; Plant Biochemistry & Physiology; International Journal of Molecular Sciences; Journal of Clinical and Medical Genomics; Environmental Analytical Chemistry; Medicinal Chemistry; Juniper publishers reivews (search for similar items in EconPapers)
Date: 2017
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Persistent link: https://EconPapers.repec.org/RePEc:adp:jomcij:v:2:y:2017:i:5:p:108-112

DOI: 10.19080/OMCIJ.2017.02.555597

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