Triethylamine → HCID 90876343、化合物

反応式

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][CH2:12][N:13]([CH3:31])[CH2:14][CH2:15][C:16]1([OH:30])[CH2:21][CH:20]2[CH2:22][CH2:23][CH:17]1[CH:18]=[C:19]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(CC)CC.[C:39](Cl)(=[O:43])[CH:40]([CH3:42])[CH3:41]>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][CH2:12][N:13]([CH3:31])[CH2:14][CH2:15][C@:16]1([O:30][C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])[CH2:21][C@H:20]2[CH2:22][CH2:23][C@@H:17]1[CH:18]=[C:19]2[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

実験手順

To a solution of 150 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol and 0.176 mL of NEt3 in 4 mL DCM 0.1 mL of isobutyrylchloride was added at 0° C. The yellow reaction mixture was stirred for 3 h at rt and then quenched with sat. aq. NaHCO3. The product was extracted with DCM, the organic phase was evaporated to dryness. The residue was dissolved in EtOAc, silica gel and a few drops of MeOH were added and the mixture was stirred vigorously for 5 h. The mixture was filtered, the filtrate evaporated and the residue purified by CC with EtOAc-MeOH (3:1) to yield 86 mg of pure rac-isobutyric acid (1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as colorless foam.