FC(F)(F)C(O)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.B([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([NH:39][C:40](=[O:50])[C:41]2[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:42]=2[CH3:49])[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=1)(O)O.CCN(CC)CC>ClCCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([NH:39][C:40](=[O:50])[C:41]3[C:42]([CH3:49])=[CH:43][C:44]([CH3:48])=[CH:45][C:46]=3[CH3:47])[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=2)[CH2:21][CH2:20]195 mg (0.207 mmol, calculated as bistrifluoroacetate salt) of crude piperidine derivative (19), 113 mg (0.621 mmol) Cu(OAc)2, 147 mg (0.415 mmol) boronic acid (6) and 1.72 ml (12.42 mmol) NEt3 were mixed in 10 ml DCE and stirred at room temperature for 20 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in methanol and subsequently submitted to reversed phase HPLC purification using a water/acetonitrile gradient containing 0.1% TFA. The required fractions were collected and lyophilized to yield (20) as white solid.
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