Synthesis of methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann rearrangement utilizing trichloroisocyanuric acid as an oxidant.
A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.
Department of Process Chemistry, Array Bio Pharma Inc., 3200 Walnut Street, Boulder, Colorado 80301, USA. zackary.crane@arraybiopharma.com
Zackary D
ZD
Crane
Paul J
PJ
Nichols
Tarek
T
Sammakia
Peter J
PJ
Stengel
D009682:Magnetic Resonance Spectroscopy; D016877:Oxidants / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D016877:Oxidants; D014753:Vinyl Compounds; C557579:methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate