96394-96-6Relevant academic research and scientific papers
Preparation of an N-sec-alkyl 2,6-disubstituted aniline: a key intermediate in the divergent synthesis of S-Metolachlor metabolites
Tyagi, Sameer,Gichinga, Moses G.,Cook, Christopher D.,Key, Jeffrey A.,McKillican, Bruce P.,Eberle, William J.,Carlin, Timothy J.,Hunt, David A.,Dowling, Alan J.
, p. 5363 - 5367 (2016/11/16)
A simple method to prepare a 2,6-disubstituted aniline containing a N-sec-alkyl group and a carbonyl on one ortho substituent is reported. This method was used to accomplish the first synthesis of side chain oxidized ethylsulfonic acid (ESA) and oxanilic acid (OXA) metabolites of S-Metolachlor (S-Moc) herbicide. The 2,6-disubstituted aniline functionality was installed by a Sugasawa reaction of readily available ortho-toluidine. The N-sec alkyl group was introduced by a Mitsunobu alkylation of the nosyl-activated 2-acetyl-6-methyl-substituted aniline. This crucial step enabled access to the key 2,6-disubstituted aniline intermediate which was used in the divergent synthesis of S-Moc metabolites. A bioinspired synthesis of the keto-ESA metabolite was achieved in one step from the hydroxyl-ESA metabolite using a ruthenium-catalyzed oxidation.[Figure presented]
