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US 4,302,391 AGranted
Unsymmetrical azetidinone aldehyde disulfides and process
AssigneeEli Lilly and Company
InventorsStjepan Kukolja, Janice L. Pfeil
Life of this patent
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Abstract
Aryl 4R[1-(2-N-3-methyl-4-al-Z-but-2-ene-oate)-2-oxo-3S-acylamino azetidinone]disulfides are prepared by reacting the corresponding 7.alpha.-acylamino-2.alpha.-alkoxy-3-methyl-3-cephem-4-carboxylates first with either phenylsulfenyl chloride or a monosubstituted-phenylsulfenyl chloride where the substituent is either chloro, methoxy, methyl or acetoxy. The disulfide compounds produced in this invention are intermediates in the synthesis of the 7.beta.-acylamino-7.alpha.-alkoxy-3-methyl 1-oxa .beta.-lactam acids, a class of antibiotic compounds.
Claims14
A compound of the formula;
- ##STR28## wherein R.sub.1 is an acyl group of the formula ##STR29## wherein R' is (a) C.sub.1 -C.sub.7 alkyl, cyanomethyl, C.sub.1 -C.sub.6 haloalkyl, 4-protected amino-4-protected carboxybutyl;
- or
- (b) C.sub.1 -C.sub.6 alkoxy, phenoxy, benzyloxy or 4-methoxybenzyloxy;
- or
- (c) the group --R" wherein R" is phenyl or substituted phenyl wherein the substituents are 1 or 2 halogens, protected hydroxy, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, protected carboxy, protected carboxymethyl, protected hydroxymethyl or protected aminomethyl;
- or
- (d) an arylalkyl group of the formula
- R"--(O).sub.m --CH.sub.2 --
- wherein R" is as defined above, and m is 0 or 1;
- or
- (e) a substituted arylalkyl group of the formula ##STR30## wherein R'" is R" as defined above, 2-thienyl, 3-thienyl, 2-furyl or 3-furyl;
- W is protected hydroxy, protected carboxy, protected amino;
- or
- (f) a heteroarylmethyl groups of the formula
- R""--CH.sub.2 --
- wherein R"" is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-thiazolyl, 5-tetrazolyl, 1-tetrazolyl;
- R.sub.2 is a carboxy protected group and R.sub.3 is phenyl or a mono-substituted phenyl group, where the substituents are chloro, methoxy, methyl, or acetoxy.
14 more elements
Dependencies are inferred from the claim text.