[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([NH:13]C(O)=O)=[CH:6]2.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])=CC=1.C[C:35]([OH:38])(C)C.[C:39]1([CH3:45])[CH:44]=CC=C[CH:40]=1>CCOC(C)=O>[C:39]([O:24][C:35]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([NH2:13])[CH2:8]1)=[O:38])([CH3:45])([CH3:44])[CH3:40]To a stirred suspension of 6-methoxy-3-carboxyaminoquinoline (Step E, 4.8 g, 0.021 mol) in toluene (109 mL) was added DPPA (5.83 mL, 0.026 mol) followed by TEA (3.6 mL, 0.026 mol). The reaction was stirred at RT for 30 min. t-BuOH (8.22 mL, 0.086 mL) was added then the mixture was heated at reflux for 8 h. The solution was diluted with EtOAc and washed 2× with a saturated solution of NH4Cl and 2× with water. The EtOAc solution was dried over MgSO4 and evaporated. The mixture was purified by flash chromatography using 20% EtOAc/hexane to give N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline.
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