Processes for making cephems from allenylazetidinone derivatives

Details Processes for making cephems from allenylazetidinone derivatives Processes for making cephems from allenylazetidinone derivatives

Filed on

1991-06-06

Date issued

1992-11-10

Examiner

Rizzo, Nicholas S.

Patent Class

Organic compounds -- part of the class 532-570 series

SubClass

Organic compounds

SubSubClass

Heterocyclic carbon compounds containing a hetero ring...

Other Related Categories

540227, 540221, C07D50102

Type

Patent

Status

active

Patent number

051625210

Description

ABSTRACT:
This invention relates to a novel process for making a cephem of formula II from 2-(3-amino-2-oxo-azetidin-1-yl)-2,3-butadienoate of formula I. In another aspect, this invention is concerned with a process of further converting a compound of formula II into an antibacterial cephem of formula III. ##STR1## In formulae I, II and III, R.sup.1 is hydrogen, a conventional amino protecting group or an acyl group; R.sup.2 is an aromatic heterocyclic or aryl group; R.sup.3 is a conventional carboxy protecting group or --CO.sub.2 R.sup.3 taken together forms a physiologically hydrolyzable ester; and R.sup.4 is a group selected from the group consisting of C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, cyclic C.sub.3-6 alkyl, and aryl; and n is 0 or 2.

REFERENCES:
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Hamashima et al., Heterocycles, "Synthesis of 3-Substituted Cephems from Penicillins via 4-Dithio-2-Azetidinone Intermediates", 5, p. 419 (1976).
Scartazzini et al., Helvetica Chimica Acta, "Neue .beta.-Lactam-Antibiotika", 58, p. 2437 (1975).
Farina et al., Journal of Organic Chemistry, "A General Route to- 3-Functionalized 3-Norcephalosporins", 54, p. 4962 (1989).
Kant et al., Tetrahedron Letters, "Reactions of Organocuprates with Vinyl Triflates and Related Cephems", 31, No. 24, p. 3389 (1990).

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