Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid.
J Med Chem
; 28(12): 1903-6, 1985 Dec.
Article
en En
| MEDLINE
| ID: mdl-2933520
ABSTRACT
The methyl and isopropyl esters of (RS)-3-benzothienylglycine were resolved with (+)- and (-)-tartaric acid in acetonitrile to give the corresponding R and S salts. The R-salt 4 was hydrolyzed to (R)-3-benzothienylglycine (5). The amino group in 5 was protected with the Boc function and the protected R amino acid 6 coupled with the p-NB ester of 7-ADCA to give the diprotected cephalosporin 7. After removal of the Boc and p-NB groups, the R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid (1) was obtained. The p-NB ester of epimeric cephalosporin 7 was separated by preparative chromatography into R and S isomers. After removal of the protective groups, the S epimer was isolated. The comparison of antibacterial activity of the R and S epimers and the RS mixture of cephalosporin 1 is reported.
Buscar en Google
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Cefalosporinas
/
Bacterias Grampositivas
Idioma:
En
Revista:
J Med Chem
Asunto de la revista:
QUIMICA
Año:
1985
Tipo del documento:
Article