N-Methylcarbazole → HCID 14697458, Verbindung
Reaktionsgleichung
CN1C2C=CC=CC=2C2C1=CC=CC=2.[S:15]([O:19][C@H:20]1[C@@H:24]([CH2:25][O:26][C:27]([O:29][CH3:30])=[O:28])[O:23][C@@H:22]([N:31]2[CH:39]=[C:37]([CH3:38])[C:35](=[O:36])[NH:34][C:32]2=[O:33])[C@@H:21]1OC(=O)C1C=CC=C(C(F)(F)F)C=1)([CH3:18])(=[O:17])=[O:16]>C(O)(C)C>[S:15]([O:19][C@H:20]1[C@@H:24]([CH2:25][O:26][C:27]([O:29][CH3:30])=[O:28])[O:23][C@@H:22]([N:31]2[CH:39]=[C:37]([CH3:38])[C:35](=[O:36])[NH:34][C:32]2=[O:33])[CH2:21]1)([CH3:18])(=[O:16])=[O:17]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A 500 mL pyrex photochemical reaction vessel equipped with a nitrogen inlet, magnetic stirrer, reflux condenser, quartz immersion well and a 450 watt medium pressure mercury-vapor immersion lamp surrounded by a uranium absorption sleeve was charged with 90% aqueous isopropyl alcohol (500 mL), N-methyl carbazole (1.46 g, 8.05 mmoles) and 1-(3-O-mesyl-5-O-(methoxycarbonyl)-2-O-(m-trifluoromethyl-benzoyl)-β-D-xylofuranosyl)thymine (3.80 g, 6.71 mmoles) from Example A3. After bubbling nitrogen through the solution for 45 minutes the solution was photolyzed for 20 hours. The solvent was concentrated to a 50 mL volume by rotary evaporation and the remaining liquid was diluted with chloroform (300 mL). The organic solution was washed with 10% aqueous NaHCO3 (2×200 ml) and the solvent was removed by rotary evaporation. The residual oil was purified by flash chromatography (3-inch diameter column containing 15 inches of flash silica gel). The column was eluted with 95:5/CHCl3 :CH3OH while collecting 125 mL fractions. Fractions 15-19 contained pure product and these fractions were concentrated in vacuo affording 1.75 g (68.9%) of 1-[2-deoxy-3-O-mesyl-5-O-methoxycarbonyl-β-D-threo-pentofuranosyl]thymine as a white crystalline solid. mp: 70°-72° C.; TLC Rf =0.51. Silica gel, CHCl3 : CH3OH/90/10