Trifluoroacetic acid → (R)-3-((S)-2-amino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane trifluoroacetate trifluoroacetate
반응식
[Br-].C(OC([NH:9][C@@H:10]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N+:16]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])=O)(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>C(Cl)Cl>[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41].[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41].[NH2:9][C@@H:10]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N+:16]([CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([CH2:17][CH2:18]2)[CH2:15]1)=[O:12].[NH2:9][C@@H:10]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N+:16]([CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([CH2:17][CH2:18]2)[CH2:15]1)=[O:12]참가 물질
4
실험 절차
To a solution of (R)-3-((S)-2-tertbutoxycarbonylamino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane bromide (I148) (0.53 mmol) in DCM (5 mL), is added trifluoroacetic acid (0.50 mL, 4.41 mmol) and the mixture stirred at RT overnight. The solvent is evaporated and the resulting crude is purified by preparative LC-MS in order to obtain the title compound as a brown gummy solid (112 mg, 43% overall yield, trifluoroacetate salt and trifluoroacetate anion, single diastereoisomer).