Process for preparing 2-acyloxymethylpenams and 3-acyloxycephams

Details Process for preparing 2-acyloxymethylpenams and 3-acyloxycephams Process for preparing 2-acyloxymethylpenams and 3-acyloxycephams

1977-12-29

1980-01-15

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544 30, 544 28, 424271, 424246, 260239A, C07D49904, C07D50102

Patent

active

041838505

ABSTRACT:
A process for preparing 2-acyloxymethylpenams and 3-acyloxycephams of the formulae 1 and 2 ##STR1## in which R represents the aliphatic, aromatic, or heterocyclic moiety of an amino-protecting group commonly employed in penicillin chemistry, R.sup.1 is hydrogen or represents a carboxy-protecting group commonly employed in penicillin chemistry, and R.sup.2 is hydrogen, C.sub.1 -C.sub.6 alkyl which may also be substituted with Cl, OCH.sub.3, or CN, and phenyl which may also be substituted with CH.sub.3, F, Cl, OCH.sub.3 or NO.sub.2, by treating an unsym-azetidinone disulfide of the formula 3 ##STR2## in which R and R.sup.1 are as defined above and R.sup.4 is benzothiazol-2-yl or benzoxazol-2-yl with silver oxide, an acid of the formula R.sup.2 COOH, and iodine, or with a silver salt of the formula R.sup.2 COOAg and iodine, or with a Simonini complex of the formula R.sup.2 COOI.R.sup.2 COOAg, to obtain a mixture of the compounds of formulae 1 and 2, and optionally separating said mixture.

REFERENCES:
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patent: 3668202 (1972-06-01), Foster et al.
patent: 3954732 (1976-05-01), Kamiya et al.
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patent: 4046761 (1977-09-01), Verweij et al.
patent: 4066641 (1978-01-01), Hamashima et al.
Morin et al., JACS 91 (1969), 1401-1407.
Kukolja et al., JACS 97 (1975), 3192-3198.
Bunce et al., Can. J. Chem. 54 (1976), 2612-2616.
Barton et al., J. Chem. Soc. (C) 1971, 3540-3550.
Micetich, Tetrahedron Letters No. 13, 1976, pp. 971-974.

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