General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent

Pieper M, Schleich H, Gröger H (2019)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (20): 3259-3263.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
In this contribution we demonstrate the feasibility of a recently developed amidation method for a general synthesis of industrially important semi-synthetic cephalosporin antibiotics starting from readily available 7-aminocephalosporanic acid and derivatives thereof. The amidation process is based on the use of 4-toluene-sulfonyl chloride as an economically attractive coupling reagent in combination with methanol or ethyl acetate as one of the solvent components. A broad reaction scope was shown by the successful synthesis of three further cephalosporin antibiotics with different functionalities, which were obtained in high yields of 82-95% in the reactions even under non-optimized conditions. It is noteworthy that also different oxime functionalities in the side chain of the 7-position are tolerated as well as an ester moiety in 4-position and a cationic functionality in 3-position. Thus, this amidation process through an activated anhydride formed by means of 4-toluenesulfonyl chloride is a broadly applicable methodology for the synthesis of industrial semi-synthetic cephalosporin antibiotics.
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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20
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3259-3263
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Pieper M, Schleich H, Gröger H. General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2019;(20):3259-3263.
Pieper, M., Schleich, H., & Gröger, H. (2019). General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(20), 3259-3263. doi:10.1002/ejoc.201900277
Pieper, M., Schleich, H., and Gröger, H. (2019). General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 3259-3263.
Pieper, M., Schleich, H., & Gröger, H., 2019. General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (20), p 3259-3263.
M. Pieper, H. Schleich, and H. Gröger, “General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, pp. 3259-3263.
Pieper, M., Schleich, H., Gröger, H.: General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 3259-3263 (2019).
Pieper, Matthias, Schleich, Herbert, and Gröger, Harald. “General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 20 (2019): 3259-3263.