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【结 构 式】

【分子编号】26579

【品名】3-hydroxy-3-[4-(methylsulfanyl)phenyl]-2-phenyl-2-[(trimethylsilyl)methyl]propanenitrile

【CA登记号】

【 分 子 式 】C20H25NOSSi

【 分 子 量 】355.57614

【元素组成】C 67.56% H 7.09% N 3.94% O 4.5% S 9.02% Si 7.9%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Reaction of benzaldehyde (I) with trimethylsilyl cyanide and ZnI2 gave O-trimethylsilyl cyanohydrin (II). Subsequent condensation of (II) with 4-(methylthio)benzaldehyde (III) in the presence of lithium hexamethyldisilazide, followed by quenching of the intermediate (IV) with KHF2 and HCl, provided benzoin (V). This was oxidized either under Swern conditions, or with Bi2O3 in acetic to afford the corresponding benzil (VI). Condensation of (VI) with trifluoroacetaldehyde ethyl hemiacetal (VII) produced imidazole (VIII). Finally, oxidation of the sulfide group of (VIII) with hydrogen peroxide in AcOH provided the target sulfone.

1 Barta, T.E.; Collins, P.W.; Weier, R.M.; Stealey, M.A.; Antiinflammatory 4,5-diarylimidazoles as selective cyclooxygenase inhibitors. Bioorg Med Chem Lett 1998, 8, 24, 3443.
2 Weier, R.M.; Collins, P.W.; Stealey, M.A.; Barta, T.E.; Huff, R.M. (Pharmacia Corp.); 4,5-Substd. imidazolyl cpds. for the treatment of inflammation. EP 0772601; US 5620999; WO 9603387 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(II) 26578 2-phenyl-3-(trimethylsilyl)propanenitrile C12H17NSi 详情 详情
(III) 18815 4-(methylsulfanyl)benzaldehyde; 4-(methylmercapto)benzaldehyde 3446-89-7 C8H8OS 详情 详情
(IV) 26579 3-hydroxy-3-[4-(methylsulfanyl)phenyl]-2-phenyl-2-[(trimethylsilyl)methyl]propanenitrile C20H25NOSSi 详情 详情
(V) 26580 2-hydroxy-2-[4-(methylsulfanyl)phenyl]-1-phenyl-1-ethanone C15H14O2S 详情 详情
(VI) 26581 1-[4-(methylsulfanyl)phenyl]-2-phenyl-1,2-ethanedione C15H12O2S 详情 详情
(VII) 26582 1-ethoxy-2,2,2-trifluoro-1-ethanol 433-27-2 C4H7F3O2 详情 详情
(VIII) 26583 methyl 4-[5-phenyl-2-(trifluoromethyl)-1H-imidazol-4-yl]phenyl sulfide C17H13F3N2S 详情 详情
Extended Information