Azetidinone derivatives and production thereof
AssigneeShionogi & Co., Ltd.
InventorsShoichiro Uyeo, Mitsuru Yoshioka, Teruji Tsuji, Ikuo Kikkawa, Wataru Nagata
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Abstract
.alpha.-[3(R)-Substituted amino-4(R)-substituted alkoxy-2-oxo-azetidin-1-yl]-.alpha.-isopropenylacetate (Ia) and .alpha.-[3(R)-substituted amino-4(R)-substituted alkoxy-2-oxo-azetidin-1-yl]-.alpha.-isopropylideneacetate (Ib) prepared from (1R,5S)-.alpha.-(3-substituted-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-e n-6-yl)-.alpha.-isopropenylacetate or (1R,5S)-.alpha.-(3-substituted-7-oxo-4-oxa-2,6-diazabicyclo-[3.2.0]hept-2- en-6-yl)-.alpha.-isopropylideneacetate with a primary alcohol in the presence of an acid. The products are useful intermediates for preparing oxadethiacephalosporins.
Claims12
A compound of the formula:
- ##STR9## wherein R.sup.1 is C.sub.1-5 alkyl, phenoxy-C.sub.1-3 alkyl, phenyl-C.sub.1-3 - alkyl, phenyl, tolyl, methoxyphenyl, chlorophenyl, nitrophenyl, hydroxyphenyl, acetoxyphenyl, acetamidophenyl, thienyl or furyl;
- R.sup.2 is ethynyl, 2-bromoethynyl, acetoxyacetyl, (1-methyl-tetrazol-5-yl)thioacetyl, (2-methyl-1,3,4-thiadiazol-5-yl)thioacetyl, 1-methylene-2-acetoxyethyl, 1-methylene-2-(1-methyltetrazol-5-yl) thioethyl, 1-methylene-2-(2-methyl-1,3,4-thiadiazol-5-yl)-thioethyl or 1-methoxycarbonylmethylene-2-(1-methyl-tetrazol-5-yl) thioethyl;
- and B is hydroxy, C.sub.1-4 alkoxy, phenyl-C.sub.1-3 alkoxy, diphenyl-C.sub.1-3 alkoxy, phenoxy, indanyloxy, naphthoxy, tri-C.sub.1-3 alkylsilyloxy, C.sub.1-3 alkoxy di-C.sub.1-3 alkylsilyloxy, tri-C.sub.1-3 alkylstannyloxy, di-C.sub.1-3 alkylhydrazino, alkali metal oxy, magnesium oxy, calcium oxy, aluminum oxy, tri-C.sub.1-3 alkylammonium oxy or bicyclohexylammonium oxy.
Dependencies are inferred from the claim text.