Process for penems

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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514192, 514195, A61K 31425, C07D49900

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active

054162084

ABSTRACT:
Antibacterial penems of formula (I), where R represents a hydrogen atom or a hydroxy protecting group, are prepared by reacting a .beta.-lactam of formula (II) with an oxalyl halide in an inert solvent in the presence of an organic or inorganic base or an acid scavenger to produce a compound of formula (III), wherein X is a halogen atom, treating the resultant compound of formula (III) with a 1,3-dioxolen-2-one of formula (IV), wherein Y is a hydroxy group, in the presence of molecular sieves or an organic or inorganic base to produce a compound of formula (V), and cyclizing the compound of formula (V) in the presence of a trialkylphosphite to provide the penems of formula (I).

REFERENCES:
patent: 4952577 (1990-08-01), Alpegiani et al.
Chemical Abstracts, vol. 102, No. 25, 24 Jun. 1985, (Columbus, Ohio, US) see p. 593, abstract No. 220862x & JP, A, 59212488 (Kyoto Pharmaceutical Industries, Ltd.) 1 Dec. 1984.
Marco Alpegiani et al, "On the Preparation of 4-Hydroxymethyl-5-Methyl-1,3-Dioxol-2-One," Synthetic Communications, 22(9), pp. 1277-1282 (May 1992).
Marco Alpegiani et al, "Synthesis and Biological Properties of FCE 25199, A New Oral Penem," The Journal of Antibiotics, vol. 45, No. 5, pp. 797-801, (May 1992).

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