Process for preparing substituted 2-thioxopenams and 2-substitut

Details Process for preparing substituted 2-thioxopenams and 2-substitut Process for preparing substituted 2-thioxopenams and 2-substitut

1983-01-25

1986-09-09

Rizzo, Nicholas S.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

514195, 540201, 540357, C07D49904, A61K 31425

Patent

active

046108238

ABSTRACT:
Disclosed is a synthesis for preparing substituted 2-thioxopenams which are useful in the synthesis of penem antibiotics 7 which may be conducted in an enantiospecific manner; said process proceeds from azetidinone 1 via the azetidinone acetic ester 2, the 4-metallothiozetidinone 3, and the 4-dithiocarbonylazetidinone 4 to the substituted 2-thioxopenam 5: ##STR1## wherein: R.sup.6 and R.sup.7 are independently selected from: hydrogen; R.sup.6 NH-- (R.sup.6 is acyl or H); substituted and unsubstituted: alkyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, and cycloalkenyl; wherein said substituents are, inter alia: halo (chloro, bromo, fluoro, iodo), hydroxyl, cyano, carboxyl, amino, and the above-recited values for R.sup.6 and R.sup.7 ; in functional terms,

REFERENCES:
patent: 4168314 (1979-09-01), Christensen
patent: 4215124 (1980-07-01), Christensen
patent: 4260618 (1981-04-01), Christensen
patent: 4443373 (1984-04-01), Girijavallabhan et al.
J. Chem. Soc. Chem. Commun. No. 13, pp. 713-714 (1982).
Jeffrey & McCombie, J. Org. Chem. 43, 587, 1982.
A. Yoshida, T. Hayoshi, N. Takeda, S. Ohda and E. Olki Chem. Pharm. Bull. 29, 2899 (1981).

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