Evolution of a Preparation Route to Sulfamoylamino Intermediates of Cephalosporin

Xudong Jiang ； Li Chen ； Xiaoling Lu ； Lan Liao ； Weiguang Wang ； Xiaocheng Huang

《International Core Journal of Engineering》 6卷3期 (2020/03) Pp. 137-140

https://doi.org/10.6919/ICJE.202003_6(3).0025

摘要

Development of a convergent preparation route to sulfamoylamino intermediates of cephalosporin is described.The target molecule is assembled through an azabicyclo [2.2.1] heptane intermediate followed by condensation reaction with sulfamoylamino methylpiperidine derivatives. The preparation of azabicyclo [2.2.1] heptane intermediate by a intramolecular condensation reaction of (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid. This avoids handling of column chromatography and l improves the overall yield and efficiency of the route.

關鍵字

Cephalosporin ； Intermediate ； Preparation ； Sulfamoylamino

參考文獻

L. Pollegioni, S. Lorenzi, E. Rosini, et al(2005). Evolution of an acylase active on cephalosporin C. Protein. Sci., vol.14, no.12, p.3064-3076.

A. E. Solh(2009). Ceftobiprole: a new broad spectrum cephalosporin . Expert Opin Pharmacotherapy, vol.10, no.10, p.1675-1686.

M. Kenji, Y. Toshio, T. Ayako, et al(2014). Structural requirements for the stability of novel cephalosporins to AmpC betalactamase based on 3D-structure. Bioorg. Med. Chem., vol.16, no.17, p.2261-2275.

R. Sharma, T.E. Park, S. Moy (2014). Ceftazidime-avibactam: a novel cephalosporin/β-lactamase inhibitor combination for the treatment of resistant Gram-negative organisms. Clin. Ther., vol.38, no.3, p.431-444.

T. Ito-Horiyama, Y. Ishii, A. Ito, et al(2014). Stability of novel siderophore cephalosporin S-649266 against clinically relevant carbapenemases. Antimicrob. Agents. Chemother., vol.60, no.7, p.4384-4386.