Hydrogen Bromide → 9-Bromo camptothecin

反応式

N([O-])=O.[Na+].[CH3:5][CH2:6][C@@:7]1([OH:31])[C:12](=[O:13])[O:11][CH2:10][C:9]2[C:14]([N:16]3[C:28](=[CH:29][C:8]1=2)[C:27]1[N:26]=[C:25]2[C:20]([C:21](N)=[CH:22][CH:23]=[CH:24]2)=[CH:19][C:18]=1[CH2:17]3)=[O:15].[BrH:32]>O>[CH3:5][CH2:6][C@@:7]1([OH:31])[C:12](=[O:13])[O:11][CH2:10][C:9]2[C:14]([N:16]3[C:28](=[CH:29][C:8]1=2)[C:27]1[N:26]=[C:25]2[C:20](=[CH:19][C:18]=1[CH2:17]3)[C:21]([Br:32])=[CH:22][CH:23]=[CH:24]2)=[O:15]

参加物

実験手順

2.15 g of NaNO2 in 40 mL of H2O were dropped at 5° C. into a solution of 9 g of 9-amino-camptothecin in 850 mL of 16% HBr. After 1 hr at room temperature the solution was dropped in a flask containing 19 g of CuBr in 200 mL of 16% HBr at 70° C. The reaction mixture was kept at 70° C. for 2 hrs, then it was poured into cold water. The precipitate was filtered and the mother liquors were extracted with CH2Cl2; the organic extract, dried and evaporated, was combined with the precipitate and purified by flash chromatography (eluent:CH2Cl2/CH3OH=95/5) to give 8.19 g of the title product (HPLC assay:97.3%).