title: Short synthesis of tert-butyl-hydroxylated 3,5-di-tert-butyl-4-hydroxybenzaldehyde: Synthesis of tert-butyl-hydroxylated S-2474.
abstract: 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.
authors.affiliation: Discovery Research Laboratories, Shionogi & Company, Ltd., Fukushima-ku, Osaka 553-0002, Japan masanao.inagaki@shionogi.co.jp
authors.forename: Masanao
authors.initials: M
authors.lastname: Inagaki
authors.forename: Saichi
authors.initials: S
authors.lastname: Matsumoto
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Tsuri
mesh_terms: 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
chemical_list: 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