C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]([O:24][C:25]([C@@H:27]1[CH2:31][C@@H:30]([OH:32])[CH2:29][C@H:28]1[C:33](=[O:45])[NH:34][C@:35]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:37][C@H:36]1[CH:38]=[CH2:39])=[O:26])([CH3:23])([CH3:22])[CH3:21].[F:46][C:47]1[CH:48]=[C:49]([C:53]2[N:62]=[C:61](O)[C:60]3[C:55](=[C:56]([CH3:66])[C:57]([O:64][CH3:65])=[CH:58][CH:59]=3)[N:54]=2)[CH:50]=[CH:51][CH:52]=1.N#N.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C.C1COCC1>[C:20]([O:24][C:25]([CH:27]1[CH2:31][CH:30]([O:32][C:61]2[C:60]3[C:55](=[C:56]([CH3:66])[C:57]([O:64][CH3:65])=[CH:58][CH:59]=3)[N:54]=[C:53]([C:49]3[CH:50]=[CH:51][CH:52]=[C:47]([F:46])[CH:48]=3)[N:62]=2)[CH2:29][CH:28]1[C:33](=[O:45])[NH:34][C:35]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:37][CH:36]1[CH:38]=[CH2:39])=[O:26])([CH3:23])([CH3:21])[CH3:22]PPh3 (787 mg, 3.0 mmol) was added to a stirred solution of the alcohol 15 (550 mg, 1.5 mmol) and the quinazolinol 127 (430 mg, 1.5 mmol) in a mixture of dry THF (40 mL) and dry DMF 10 mL. The reaction mixture was put under inert atmosphere (N2) at room temperature and DIAD (591 μL, 3.0 mmol) was added. The reaction mixture was stirred for 18 h whereafter the solvents were evaporated. The residue was dissolved in CHCl3 and washed with brine in a separatory funnel. The organic phase was dried with Na2SO4, evaporated on silica and purified by flash chromatography (heptane:ethyl acetate 2:1 to 1:1) which gave the title compound as a white-beige solid (896 mg, 94%), LRMS (M+H) 634.
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