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【结 构 式】 
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【分子编号】27869 【品名】(1S)-1-[(2R)-2-(2-fluorophenyl)oxiranyl]ethyl trifluoromethanesulfonate 【CA登记号】 |
【 分 子 式 】C11H10F4O4S 【 分 子 量 】314.2576128 【元素组成】C 42.04% H 3.21% F 24.18% O 20.36% S 10.2% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Treatment of epoxyalcohol (IX) with trifluoromethanesulfonic anhydride and diisopropyl ethylamine gave triflate (XIII). Condensation of (XIII) with imidazolone (IV) provided the required N-alkylated compound (XIV) along with some O-alkylated isomer, which were separated by column chromatography. Epoxide opening with triazole (XV) afforded the imidazolone (XVI), which was finally hydrogenated to produce the target imidazolidinone. Alternatively, condensation of triflate (XIII) with imidazolidinone (V) furnished, after chromatographic separation of some O-alkylated isomer, imidazolidinone (XVII). Finally, the reaction of (XVII) with triazole (XV) then provided an alternative route to the target compound.
| 【1】 Itoh, K.; Tamura, N.; Matsushita, Y.; Hososno, H.; Hayashi, R.; Okonogi, K.; Kitazaki, T.; Tasaka, A.; Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones. Chem Pharm Bull 1999, 47, 3, 351. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 27860 | 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one | C11H8F4N2O2 | 详情 | 详情 | |
| (V) | 27861 | 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-imidazolidinone | C11H10F4N2O2 | 详情 | 详情 | |
| (IX) | 27865 | (1S)-1-[(2R)-2-(2-fluorophenyl)oxiranyl]-1-ethanol | C10H11FO2 | 详情 | 详情 | |
| (XIII) | 27869 | (1S)-1-[(2R)-2-(2-fluorophenyl)oxiranyl]ethyl trifluoromethanesulfonate | C11H10F4O4S | 详情 | 详情 | |
| (XIV) | 27870 | 1-[(1R)-1-[(2S)-2-(2-fluorophenyl)oxiranyl]ethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one | C21H17F5N2O3 | 详情 | 详情 | |
| (XV) | 13135 | 1H-1,2,4-Triazole; 1,2,4-Triazole | 288-88-0 | C2H3N3 | 详情 | 详情 |
| (XVI) | 27871 | 1-[(1R,2R)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one | C23H20F5N5O3 | 详情 | 详情 | |
| (XVII) | 27872 | 1-[(1R)-1-[(2S)-2-(2-fluorophenyl)oxiranyl]ethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-imidazolidinone | C21H19F5N2O3 | 详情 | 详情 |