2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 70148942、化合物

反応式

[Na].[C:2]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[F:25][C:26]([F:37])([F:36])[CH2:27]OS(C(F)(F)F)(=O)=O>CN(C)C=O>[C:2]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:17]([CH2:27][C:26]([F:37])([F:36])[F:25])[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

参加物

実験手順

Add to a suspension of sodium hydrdide (0.029 g, 1.21 mmol) in anhydrous dimethylformamide (5 mL) a suspension of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan (0.38 g, 1.2 mmol, Preparation 9) in anhydrous dimethylformamide (7 mL). Stir for 3 hours at room temperature and add a large excess of 1,1,1-trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester. Stir overnight at room temperature, quench the reaction with water, wash the organic phase with water, dry (MgSO4), filter and concentrate in vacuo to afford 4-[1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester. Repeat this preparation using 2.88 mmol of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan. Combine the product from both reactions and purify by column chromatography on silica gel eluting with 30% ethyl acetate in hexane and concentrate the appropriate fractions to afford 0.48 g of 4-[1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester.