[OH:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16].CCOC(C)=O>CN(C=O)C.C1COCC1.[Cl-].[Na+].O>[OH:1][NH:2][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[C:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1
HONH2 (50% aqueous, 0.3 mL) was added to IV (32 mg, 0.1 mmol) in DMF (0.3 mL) and THF (0.3 mL) at 0° C. The reaction mixture was stirred at rt for 17 h, after which brine (3 mL) and EtOAc (3 mL) were added. The phases were separated, and the aqueous phase was extracted with EtOAc (2×3 mL). The organic phases were then combined, dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:3 to 100:10) as eluant to furnish V, a colourless oil (9.6 mg, 30%).
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