C(OC([NH:8][C@H:9]([C:22]([NH:24][C@H:25]([C:27]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:44]([C:45]#[N:46])=[C:43]([S:47][CH2:48][C:49]3[N:50]=[C:51]([C:54]4[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=4)[S:52][CH:53]=3)[N:42]=[C:41]([N:61]3[CH2:64][CH2:63][CH2:62]3)[C:40]=2[C:65]#[N:66])=[CH:35][CH:34]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=O)(C)(C)C.[F:67][C:68]([F:73])([F:72])[C:69]([OH:71])=[O:70]>ClCCl>[F:67][C:68]([F:73])([F:72])[C:69]([OH:71])=[O:70].[F:67][C:68]([F:73])([F:72])[C:69]([OH:71])=[O:70].[NH2:8][C@H:9]([C:22]([NH:24][C@H:25]([C:27]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:44]([C:45]#[N:46])=[C:43]([S:47][CH2:48][C:49]3[N:50]=[C:51]([C:54]4[CH:55]=[CH:56][C:57]([Cl:60])=[CH:58][CH:59]=4)[S:52][CH:53]=3)[N:42]=[C:41]([N:61]3[CH2:62][CH2:63][CH2:64]3)[C:40]=2[C:65]#[N:66])=[CH:35][CH:34]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]180 mg (0.188 mmol) of 2-{4-(2-(azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate (Example 3A) were initially charged in 5 ml dichloromethane. 1.0 ml (12.98 mmol) of trifluoroacetic acid was added, and the reaction solution was then stirred at RT for 30 min. The reaction solution was concentrated by evaporation and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 153 mg (83% of theory) of the target compound.
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