反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH:10]([OH:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1.C(N([CH2:21][CH3:22])CC)C.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>C(Cl)(Cl)Cl>[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:21][CH:22]=1)[C:28]([O:15][CH:10]([CH2:9][N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:24]([F:35])([F:34])[F:23])[CH:26]=1)[C:11]([F:12])([F:14])[F:13])=[O:29]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
The 3-[(3-fluorophenyl)amino]-1,1,1-trifluoro-2-propanol (446 mg, 2.0 mmol) from EX-662A and triethylamine (544 mg) were dissolved in anhydrous CHCl3 (30 mL) and cooled to 0° C. Then a solution of 3-trifluoromethylbenzoyl chloride (1.04 g, 5.0 mmol) in anhydrous CHCl3 (6 mL) was added over a period of 15 min. The solution was stirred at room temperature. After 14 h, the solution was washed with 5% NaHCO3 (2×20 mL) and brine (2×10 mL), and then dried over anhydrous MgSO4. Removal of the solvent in vacuo gave 832 mg (73%) of the desired 2,2,2-trifluoro-1-[[(3-fluoro-phenyl)[3-(trifluoromethyl)benzoyl]amino]methyl]ethyl 3-trifluoromethyl-benzoate product as an amber oil, which was greater than 95% pure by reverse phase HPLC analysis. 1H NMR (CDCl3) δ7.25-8.39 (m, 9H), 7.02 (q, 1H), 6.71 (m, 2H), 6.11 (m, 1H), 4.58 (dd, 1H), 4.35 (dd, 1H). 19F NMR (CDCl3) δ−64.4 (m, 6F), −77.4 (s, 3F), −111.3 (m, 1F). HRMS calcd. for C25H15F10NO3: 568.0970 [M+H]+, found: 568.0968.
後処理
- washthe solution was washed with 5% NaHCO3 (2×20 mL) and brine (2×10 mL)
- dry with materialdried over anhydrous MgSO4
- customRemoval of the solvent in vacuo
出典と根拠
- ORDレコード
- ord-c74cdf4c5ca84d5e928b959b06210e26
- 出典データセット
- uspto-grants-2004_03
- 特許番号
- US06699898B2
関連ノート
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