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【结 构 式】

【分子编号】56170

【品名】methyl 4-methylphenyl sulfoxide; methyl(4-methylphenyl)oxo-lambda~4~-sulfane

【CA登记号】

【 分 子 式 】C8H10OS

【 分 子 量 】154.2328

【元素组成】C 62.3% H 6.54% O 10.37% S 20.79%

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:(IX)

Condensation of isobutyrophenone (IV) with the lithium derivative of (S)-methyl p-tolyl sulfoxide (IX) produced alcohol (X) as a diastereomeric mixture. After chromatographic separation of the desired diastereoisomer, the methylsulfanyl group was selectively oxidized to sulfone (XI) with m-chloroperbenzoic acid. Reduction of the tolyl sulfoxide moiety of (XI) by means of NaI in the presence of acetyl chloride led to the corresponding sulfide (XII). Cyclization of the hydroxy sulfide (XII) to epoxide (XIII) was accomplished via S-alkylation with triethyloxonium tetrafluoroborate. Finally, opening of the chiral epoxide (XIII) with triazole (XIV) in the presence of K2CO3 furnished the title compound.

1 Tokizawa, M.; Kanamaru, Y.; Matsumoto, M.; Asaoka, T.; Matsuda, H.; Kuraishi, T.; Maebashi, K.; Taido, N.; Kawahara, R. (SSP Co., Ltd.); Triazole derivs.. EP 0435081; JP 1991223266; US 5147886 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Xa) 56171 (2R)-3-methyl-1-[(4-methylphenyl)sulfinyl]-3-(methylsulfanyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol C20H23F3O2S2 详情 详情
(Xb) 56172 (2S)-3-methyl-1-[(4-methylphenyl)sulfinyl]-3-(methylsulfanyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol C20H23F3O2S2 详情 详情
(IV) 56166 2-methyl-2-(methylsulfanyl)-1-[4-(trifluoromethyl)phenyl]-1-propanone C12H13F3OS 详情 详情
(IX) 56170 methyl 4-methylphenyl sulfoxide; methyl(4-methylphenyl)oxo-lambda~4~-sulfane C8H10OS 详情 详情
(XI) 56173 (2R)-3-methyl-1-[(4-methylphenyl)sulfinyl]-3-(methylsulfonyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol C20H23F3O4S2 详情 详情
(XII) 56174 (2R)-3-methyl-1-[(4-methylphenyl)sulfanyl]-3-(methylsulfonyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol C20H23F3O3S2 详情 详情
(XIII) 56175 methyl 1-methyl-1-{(2R)-2-[4-(trifluoromethyl)phenyl]oxiranyl}ethyl sulfone; (2R)-2-[1-methyl-1-(methylsulfonyl)ethyl]-2-[4-(trifluoromethyl)phenyl]oxirane C13H15F3O3S 详情 详情
(XIV) 13135 1H-1,2,4-Triazole; 1,2,4-Triazole 288-88-0 C2H3N3 详情 详情
Extended Information