Short synthesis of tert-butyl-hydroxylated 3,5-di-tert-butyl-4-hydroxybenzaldehyde: Synthesis of tert-butyl-hydroxylated S-2474.
We have developed a very short synthesis of tert-butyl-hydroxylated di-tert-butyl-4-hydroxybenzaldehyde in which the HBr-DMSO system is used as an effective oxidant (overall yield of 45% for the entire four-step process from 2-tert-butyl-p-cresol). We also accomplished the synthesis of a major metabolite of the antiarthritic drug candidate S-2474.
Inagaki
Masanao
M
Discovery Research Laboratories, Shionogi & Company, Ltd., Fukushima-ku, Osaka 553-0002, Japan masanao.inagaki@shionogi.co.jp
Matsumoto
Saichi
S
Tsuri
Tatsuo
T
D000975:Antioxidants / Q000737:chemistry* / Q000378:metabolism; D018501:Antirheumatic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002084:Butylated Hydroxytoluene / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D003499:Cyclic S-Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C409872:((E)-(5)-(3,5-di-tert-butyl-4-hydroxybenzylidene)- 2-ethyl-1,2-isothiazolidine-1,1-dioxide); D000975:Antioxidants; D018501:Antirheumatic Agents; D001547:Benzaldehydes; D003499:Cyclic S-Oxides; D013844:Thiazoles; C475738:tert-butyl-hydroxylated 3,5-di-tert-butyl-4-hydroxybenzaldehyde; D002084:Butylated Hydroxytoluene