Journal of Organic Chemistry p. 3907 - 3913 (1989)
Update date:2022-08-05
Topics:
Blacklock, Thomas J.
Butcher, John W.
Sohar, Paul
Rothauser Lamanec, Theresa
Grabowski, Edward J. J.
A four-step synthesis of the human leukocyte elastase (HLE) inhibitor 1,1-dioxo-trans-7-methoxycephalosporanic acid tert-butyl ester in 44percent isolated yield from 7-aminocephalosporanic acid (7-ACA) is described.A variety of 7-substituents have been introduced via metal-catalyzed diazo insertion reactions, and the use of a flow reactor for chemodiscriminate control of particularly rapid reactions is presented.A chemoselective oxidation of 7-ACA tert-butyl ester to the corresponding 1,1-dioxide without formal N-protection is introduced.
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