N-Acetylserotonin → 3-[2-(acetylamino)ethyl]-1H-indol-5-yl 4-nitrophenyl carbonate

반응식

[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].CN1CCOCC1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>O1CCCC1>[C:25](=[O:26])([O:27][C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=1)[O:16][C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[NH:9][CH:8]=[C:7]2[CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1]

참가 물질

실험 절차

To N-acetylserotonin (0.9 g; 4 mmol) was added N-methylmorpholine (0.92 ml, 8 mmol), and 4-nitrophenyl chloroformate (1.61 g; 8 mmol) dissolved in tetrahydrofuran. Reaction was carried out for 0.5 h under an argon atmosphere. The solvent was evaporated. The residue was purified by column chromatography (SiO2, methanol/methylene chloride) to give 0.92 g (yield 60%) of crystalline yellow product with a melting point 153-156° C.