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ChemInform Abstract: Synthesis of HR 916 K: An Efficient Route to the Pure Diastereomers of the 1-(Pivaloyloxy)ethyl Esters of Cephalosporins.

✍ Scribed by E. DEFOSSA; G. FISCHER; U. GERLACH; R. HOERLEIN; D. ISERT; N. KRASS; R. LATTRELL; U. STACHE; T. WOLLMANN

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of HR 916 K: An Efficient Route to the Pure Diastereomers of the 1-(Pivaloyloxy)ethyl Esters of Cephalosporins.

-Diastereomerically pure HR 916 K (VI), the 1(S)-pivaloyloxyethyl prodrug ester of the cephalosporin cefdaloxime, is synthesized and separated from the (R) diastereomer as HCl salt. The undesired (R) diastereomer is recycled by acidic saponification or enzymatic cleavage to (I).

πŸ“œ SIMILAR VOLUMES

Synthesis of HR 916 K: An Efficient Rout
Synthesis of HR 916 K: An Efficient Route to the Pure Diastereomers of the 1-(Pivaloyloxy)ethyl Esters of Cephalosporins
✍ Defoßa, Elisabeth ;Fischer, Gerd ;Gerlach, Uwe ;HΓΆrlein, Rolf ;Isert, Dieter ;Kr πŸ“‚ Article πŸ“… 1996 πŸ› John Wiley and Sons 🌐 English βš– 774 KB

## Abstract HR 916 K (5), the 1‐(__S__)‐(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, exhibits a significantly higher oral bioavailability than the 1‐(__R__) diastereomer HR 916 J. An efficient synthesis of HR 916 K was developed. The separation of the diastereomers was achieve

Synthesis of HR 916 B: The First Technic
Synthesis of HR 916 B: The First Technically Feasible Route to the 1-(Pivaloyloxy)ethyl Esters of Cephalosporins
✍ Fleischmann, Klaus ;Adam, Friedhelm ;DΓΌrckheimer, Walter ;Hertzsch, Winfried ;HΓΆ πŸ“‚ Article πŸ“… 1996 πŸ› John Wiley and Sons 🌐 English βš– 892 KB

## Abstract An efficient synthesis of HR 916 B (4), the orally active 1‐(__RS__)‐(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, was developed and applied on a multi‐kg scale. AMCA (8) was prepared by exchange of the acetoxy group of fermentation product ACA (7) with the nucleoph