N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamino)-4-oxo-azetidines and process

A compound of the formula ##STR54## wherein, M is hydrogen or is a lithium, potassium, sodium, ammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, tributylammonium, trimethylammonium, triethylammonium, tribenzylammonium, trihexylammonium, trimethylphenylammonium or triphenylammonium;

• R.sub.1 is hydrogen, a carboxylic acid protecting group, lithium, potassium, sodium, ammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, tributylammonium, trimethylammonium, triethylammonium, tribenzylammonium, trihexylammonium, trimethylphenylammonium or triphenylammonium;
• R.sub.2 is
• a. C.sub.1 to C.sub.7 alkyl, C.sub.3 to C.sub.7 alkenyl, chloromethyl, dichloromethyl, 4-carboxybutyl, 4-formylbutyl, 4-amino-4-carboxybutyl, 4-formylbutyl, 4-amino-4-carboxybutyl, 4-protected carboxybutyl, or 4-protected amino-4-protected carboxybutyl;
• or
• b. C.sub.1 to C.sub.6 alkoxy, C.sub.3 to C.sub.6 cycloalkyloxy, benzyloxy or substituted benzyloxy, wherein the substituents are one to three groups chosen from the group consisting of C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy or chloro;
• or
• c. 1,4-cyclohexadienyl, phenyl or substituted phenyl, wherein the substituents are one or two groups chosen from the group consisting of chlorine, bromine, hydroxy, trifluoromethyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, carboxymethyl, hydroxymethyl, aminomethyl and protected aminomethyl;
• or
• d. a group of the formula
• R'--(O).sub.m --CH.sub.2 --
• wherein R' is 1,4-cyclohexadienyl, phenyl or substituted phenyl as defined above, and m is 0 or 1;
• or
• e. a group of the formula ##STR55## wherein R" is R' as defined above, 2-thienyl, or 3-thienyl;
• W is hydroxy, carboxy, protected carboxy, amino or protected amino;
• or
• f. a heteroarylmethyl group of the formula
• R'"--CH.sub.2 --
• wherein R'" is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-thiazolyl, 5-tetrazolyl or 1-tetrazolyl;
• with the limitation that when the compound is of the formula ##STR56## R.sub.2 is 1,4-cyclohexadienyl, phenyl or substituted phenyl, wherein the substituents are one or two groups chosen from the group consisting of chlorine, bromine, hydroxy, trifluoromethyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, carboxymethyl, hydroxymethyl, aminomethyl and protected aminomethyl.