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Kukolja S, Pfeil JL, Draheim SE, et al. Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid. J Med Chem. 1985;28(12):1903-6doi: 10.1021/jm00150a024.
Kukolja, S., Pfeil, J. L., Draheim, S. E., & Ott, J. L. (1985). Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid. Journal of medicinal chemistry, 28(12), 1903-6. https://doi.org/10.1021/jm00150a024
Kukolja, S, et al. "Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid." Journal of medicinal chemistry vol. 28,12 (1985): 1903-6. doi: https://doi.org/10.1021/jm00150a024
Kukolja S, Pfeil JL, Draheim SE, Ott JL. Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid. J Med Chem. 1985 Dec;28(12):1903-6. doi: 10.1021/jm00150a024. PMID: 2933520.
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J Med Chem. 1985 Dec;28(12):1903-6. doi: 10.1021/jm00150a024.

Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid.

Journal of medicinal chemistry

S Kukolja, J L Pfeil, S E Draheim, J L Ott

PMID: 2933520 DOI: 10.1021/jm00150a024

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.

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