Cl.[O:2]=[C:3]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[CH2:16][CH2:15][CH2:14][NH:13][C:12]=3[N:11]=2)[CH2:6][CH2:5][N:4]1[CH2:20][C:21]([OH:23])=O.CN1CCOCC1.[CH3:31][C:32]#[N:33].F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49]C=2N=N1.[CH3:61][CH2:62][O:63][C:64](C)=[O:65]>>[CH2:62]([O:63][C:64](=[O:65])[CH2:31][C@@H:32]([C:48]1[CH:49]=[N:41][CH:45]=[CH:46][CH:47]=1)[NH:33][C:21](=[O:23])[CH2:20][N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[CH2:16][CH2:15][CH2:14][NH:13][C:12]=3[N:11]=2)[C:3]1=[O:2])[CH3:61]To a stirred solution of 2-8 (50 mg, 0.15 mmol), 2-10 (44 mg, 0.17 mmol) (Rico et al., J. Org. Chem., 1993, 58, 7948), NMM (83 μL, 0.75 mmol), and CH3CN (1 mL) was added BOP (74 mg, 0.17 mmol). After 20 h, the reaction mixture was diluted with EtOAc and then washed with sat. NaHCO3, H2O and brine, dried (MgSO4), and concentrated to give 2-12 as a brown oil.
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