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US 4,175,076 AGranted
Azetidinone mercury sulfides and process therefor
AssigneeEli Lilly and Company
InventorLowell D. Hatfield
Life of this patent
Estimating the term…
Abstract
Novel azetidinone mercury sulfides are prepared by the reaction of penicillin derived thiazolineazetidinones with a mercuric halide in the presence of an alcohol or glycol. They are useful intermediates in the preparation of cephalosporin compounds.
Claims10
A process for preparing a compound of the formula ##STR9## by reacting a compound of the formula ##STR10## with about 1.0 to about 1.2 equivalents of a mercuric halide of the formula HgX.sub.2 in an inert organic solvent in the presence of at least about an equivalent amount of a C.sub.1 to C.sub.8 primary or secondary alcohol or C.sub.1 -C.sub.8 diol
- wherein in the above formulas n is 1 or 0, X is chloro or bromo, R is hydrogen or a carboxylic acid ester protecting group and R.sub.1 is
- (a) C.sub.1 -C.sub.4 alkyl or halo-C.sub.1 -C.sub.4 alkyl;
- (b) benzyloxy, 4-nitrobenzyloxy, 2,2,2-trichloroethoxy, tert-butoxy, benzhydryloxy, 4-methoxybenzyloxy;
- (c) the group R.sub.2 wherein R.sub.2 is 1,4-cyclohexadienyl, phenyl or phenyl substituted with 1 or 2 substituents selected from the group consisting of chloro, bromo, iodo, hydroxy, nitro, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
- (d) an arylalkyl group of the formula
- R.sub.2 --(O).sub.m --CH.sub.2 --
- wherein R.sub.2 is as defined above and m is 0 or 1;
- or
- (e) a heteroarylmethyl group of the formula
- R.sub.3 CH.sub.2 --
- wherein R.sub.3 is 2-thienyl, 3-thienyl, 2-furyl, 2-thiazolyl, 5-tetrazolyl, 1-tetrazolyl, or 4-isoxazolyl.
8 more elements
Dependencies are inferred from the claim text.