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US 4,855,418 AGranted
Process for production of ceophalosporins
AssigneeEli Lilly and Company
InventorsGwendolyn K. Cook, John H. McDonald, III
Life of this patent
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Abstract
Cephalosporin and 1-carba(1-dethia)cephalosporin antibiotics substituted in the 3-position with, inter alia, alkyl, alkenyl and alkynyl, are provided via process comprising conversion of a cephalosporin or 1-carba(1-dethia)-3-cephem substituted in the 3-position with halogen or a sulfonyloxy ester with Pd(O) mediated alkylation with organostannanes.
Claims16
A process for preparing a compound of the formula ##STR16## wherein A is a protected amino group or an acylamino group R(CO)--NH--;
- R.sub.1 is a carboxy-protecting group or a biologically-labile ester;
- X is sulfur or --CH.sub.2 --;
- and R.sub.2 is methyl, C.sub.2 -C.sub.6 alkenyl;
- C.sub.2 -C.sub.6 alkynyl;
- C.sub.1 -C.sub.6 substituted alkyl, C.sub.2 -C.sub.6 substituted alkenyl;
- C.sub.2 -C.sub.6 substituted alkynyl;
- phenyl;
- substituted phenyl;
- C.sub.1 -C.sub.6 alkyloxymethyl;
- phenyl-C.sub.1 -C.sub.6 alkyloxymethyl;
- or tri(C.sub.1 -C.sub.6)alkylsilyloxymethyl;
- which comprises reacting a compound of the formula ##STR17## wherein A, X and R.sub.1 are as defined above, and R.sub.3 is trifluoromethylsulfonyloxy, methanesulfonyloxy, toluenesulfonyloxy, chloro, bromo or iodo;
- in an inert solvent in the presence of palladium(O) and, when R.sub.3 is trifluoromethanesulfonyloxy, methanesulfonyloxy or p-toluenesulfonyloxy in the presence of an alkali metal halide, with a tin transfer reagent of the formula trialkyl(C.sub.1 -C.sub.6)alkyl--SN--R.sub.2 or SN(R.sub.2).sub.4, wherein R.sub.2 has the same meanings as defined above.
10 more elements
Dependencies are inferred from the claim text.