Intermediates for preparing cephalosporins and methods of production
AssigneeAmerican Home Products Corporation
InventorCharles A. Robinson
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Abstract
.DELTA..sup.3 -CEPHALOSPORINS ARE PREPARED BY REACTING NOVEL DIORGANODIHALOSILANE OR MONORGANODIHALOSILANE DERIVATIVES OF 7-AMINOCEPHALOSPORANIC ACID ("7ACA") and 7-amino-desacetoxycephalosporanic acid ("7ADCA") with known acylating agents followed by hydrolysis or alcoholysis to produce .DELTA..sup.3 -cephalosporins with useful antibiotic activity. The dialkyldihalosilane derivatives are prepared by adding a base such as triethylamine slowly to a mixture of 7ACA or 7ADCA and a dialkyldihalosilane.
Claims13
A compound of the group consisting of those having the following formula:
- ##EQU8## wherein:
- R.sup.1 is of the group consisting of hydrogen, lower alkyl, phenyl, loweralkylphenyl and benzyl
- R.sup.2 is of the group consisting of lower alkyl, phenyl, loweralkylphenyl and benzyl
- R.sup.3 is hydrogen or ##EQU9## R.sup.a is of the group consisting of hydrogen, 2-thienylacetyl, phenylglycyl, dihydrophenylglycyl, 2-furylacetyl, phenylglycolyl, phenylacetyl and phenoxyacetyl;
- W is of the group consisting of hydrogen and ##EQU10## wherein R.sup.1 and R.sup.2 have the same meaning as before, and X is halogen;
- m and p are integers from 0 to 1 and are always equal
- n is an integer from 1 to about 25;
- Y is of the group consisting of halogen, and groups of the following formula:
- ##EQU11## wherein R.sup.a has the same meaning as before;
- with the provisos that, in Formula I,
- 1. when m is o and p is O, n is more than 1;
- 2. when n is more than 1, the moieties A of the additional groups B recur in ramdom head-toward-head, head-toward-tail and tail-toward-tail disposition;
- 3. when W is hydrogen, n is 1, and Y is Formula III, then R.sup.a is hydrogen
- 4 when W is hydrogen or ##EQU12## Y is not halogen when n is 1.
A process for preparing organosilane derivatives of 7ACA or 7 ADCA which compriss:
- reacting 7-ACA or 7ADCA with a dihalosilane of the following formula ##EQU14## wherein:
- R.sup.1 is of the group consisting of hydrogen, lower alkyl, phenyl, loweralkylphenyl and benzyl;
- R.sup.2 is of the group consisting of lower alkyl, phenyl, loweralkylphenyl and benzyl and X is halogen in an anhydrous non-hydroxylic organic solvent in the presence of an acid acceptor present in amounts not greater than two equivalents per mole of dihalosilane wherein the acid acceptor is added slowly to a mixture of 7-ACA or 7-ADCA and said dihalosilane.
A process according to claim 10 wherein the acylated product of claim 26 is treated to a process selected from the group consisting of hydroylsis and alcoholysis to obtain the corresponding .DELTA..sup.3 -cephalosporin.
Dependencies are inferred from the claim text.