Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil.

Pieper M, Schleich H, Gröger H (2019)
The Journal of antibiotics 72(9): 702-708.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Abstract / Bemerkung
In the synthesis of cephalosporin antibiotics, esterified in 4-position, the ∆2-isomerization is a well-known side reaction proceeding under basic conditions. In this work, we investigated the ∆2-isomerization of the esterified cefpodoxime proxetil. Due to the R-configuration and S-configuration of the stereogenic center in the side chain in 4-position, there are two starting materials being diastereomeric to each other. Furthermore, an additional stereogenic center is formed in the isomerization step, thus leading to four possible products. To the best of our knowledge, in this work for the first time the ∆2-isomerization of the two isolated diastereomers of AMCA proxetil, a precursor of cefpodoxime proxetil, as a starting material is reported. It has been shown, that each diastereomer only reacts to one of the two possible ∆2-diastereomers. The synthesis, isolation and characterization of (R)-diastereomers as well as (S)-diastereomers of ∆2-AMCA proxetil and cefpodoxime proxetil, respectively, are presented.
Erscheinungsjahr
2019
Zeitschriftentitel
The Journal of antibiotics
Band
72
Ausgabe
9
Seite(n)
702-708
ISSN
0021-8820
Page URI
https://pub.uni-bielefeld.de/record/2936254

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Pieper M, Schleich H, Gröger H. Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil. The Journal of antibiotics. 2019;72(9):702-708.
Pieper, M., Schleich, H., & Gröger, H. (2019). Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil. The Journal of antibiotics, 72(9), 702-708. doi:10.1038/s41429-019-0190-z
Pieper, M., Schleich, H., and Gröger, H. (2019). Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil. The Journal of antibiotics 72, 702-708.
Pieper, M., Schleich, H., & Gröger, H., 2019. Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil. The Journal of antibiotics, 72(9), p 702-708.
M. Pieper, H. Schleich, and H. Gröger, “Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil.”, The Journal of antibiotics, vol. 72, 2019, pp. 702-708.
Pieper, M., Schleich, H., Gröger, H.: Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil. The Journal of antibiotics. 72, 702-708 (2019).
Pieper, Matthias, Schleich, Herbert, and Gröger, Harald. “Isolation and characterization of side-products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil.”. The Journal of antibiotics 72.9 (2019): 702-708.

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