|
【结 构 式】 
|
【分子编号】56736 【品名】3-amino-1,1,1-trifluoro-2-propanol 【CA登记号】431-38-9 |
【 分 子 式 】C3H6F3NO 【 分 子 量 】129.0819896 【元素组成】C 27.91% H 4.69% F 44.15% N 10.85% O 12.39% |
合成路线1
该中间体在本合成路线中的序号：(IX)The intermediate mixed anhydride (V) has been obtained as follows: the condensation of 2-nitroimidazole (I) with methyl 2-bromoacetate (II) by means of NaOMe in methanol gives 2-(2-nitro-1H-imidazol-1-yl)acetic acid methyl ester (III), which is hydrolyzed with NaOH to yield the corresponding acid (IV). Finally, this compound is condensed with isobutyl chloroformate by means of NMM in THF to afford the desired mixed anhydride intermediate (V). The condensation of 2,2,2-trifluoroacetaldehyde ethyl hemiacetal (VI) with nitromethane (VII) by means of K2CO3 gives 1,1,1-trifluoro-3-nitro-2-propanol (VIII), which is reduced with H2 over RaNi in ethanol to yield 3-amino-1,1,1-trifluoro-2-propanol (IX). Finally, this compound is condensed with the mixed anhydride intermediate (V) by means of NMM in THF to afford the target amide.
| 【1】 Tracy, M.; Kelson, A.B.; Workman, P.; Lewis, A.D.; Aboagye, E.O. (Cancer Research UK; SRI International); Fluorinated 2-nitroimidazole analogs for detecting hypoxic tumor cells. EP 0775117; JP 1998506104; US 5721265; WO 9604249 . |
| 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) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (II) | 12309 | methyl 2-bromoacetate; methyl bromoacetate | 96-32-2 | C3H5BrO2 | 详情 | 详情 |
| (III) | 10258 | methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate | 22813-31-6 | C6H7N3O4 | 详情 | 详情 |
| (IV) | 56733 | 2-(2-nitro-1H-imidazol-1-yl)acetic acid | C5H5N3O4 | 详情 | 详情 | |
| (V) | 56734 | C10H13N3O6 | 详情 | 详情 | ||
| (VI) | 26582 | 1-ethoxy-2,2,2-trifluoro-1-ethanol | 433-27-2 | C4H7F3O2 | 详情 | 详情 |
| (VII) | 39563 | nitromethane | 75-52-5 | CH3NO2 | 详情 | 详情 |
| (VIII) | 56735 | 1,1,1-trifluoro-3-nitro-2-propanol | C3H4F3NO3 | 详情 | 详情 | |
| (IX) | 56736 | 3-amino-1,1,1-trifluoro-2-propanol | 431-38-9 | C3H6F3NO | 详情 | 详情 |