Diisopropylethylamine → HCID 86589980, compound

Participants

Reaction Steps

4′-C-Aminomethylthymidine (4) (0.14 mmol) was dissolved in anhydrous N,N-dimethylformamide (1 mL). N-Trifluoroacetylglycine (0.036 g, 0.21 mmol) and O-(N-succimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate [TSTU] (0.085, 0.28 mmol) were then added and the solution stirred at ambient temperature. Diisopropylethylamine (0.036 g, 0.28 mmol, 0.05 mL) was then added dropwise to the solution with stirring. After 12 hours the solvent was removed under vacuum and the residue redissolved in dichloromethane:methanol (9:1). Applied solution directly to a silica gel column and eluted with dichloromethane:methanol (9:1). Fractions containing the desired material were pooled and the solvent removed under vacuum to give the title compound (5) as a clear, glassy material (0.28 g, 28% from crude 4). δH(300 MHz, CD3OD) 7.91(1H, s, H-6), 6.27(1H, dd, H-1′), 4.49(1H, dd, H-3′), 3.74(2H, s, glycyl CH2), 3.52(1H, d, H-5′), 3.51(2H, s, 4′-C—CH2), 3.43(1H, d, H-5′), 2.32(2H, m, H-2′), 1.68(3H, s, 5-CH3); ES +ve m/z 425(M+H)+, 442(M+H2O)+, 447(M+Na)+.

Provenance & Evidence