Methyl D-Tryptophanate → 3-Azido-3-deoxythymidine 5-methoxy-D-trytophanyl-phosphoramidate

Participants

Reaction Steps

Compound 40 (312 mg, 0.721 mmol) and D-tryptophan methyl ester (HCl salt, 367 mg, 1.44 mmol) were subjected to a procedure similar to that described in Example 6. Flash chromatography (SiO2, 5:2:0.25 CHCl3/MeOH/H2O containing 0.5% conc. NH4OH) gave the title compound (256 mg, 63%) as a white solid. 1H NMR (D2O, 300 MHz) 7.299 (d, J=7.9 Hz, 1H), 7.182 (d, J=8.1 Hz, 1H), 7.141 (s, 1H), 6.939 (s, 1H), 6.930 (dd, J=7.0, 8.1 Hz, 1H), 6.816 (t, J=7.0 7.9 Hz, 1H), 5.773 (t, J=6.8 Hz, 1H), 3.851-3.741 (m, 2H), 3.691 (m, 1H), 3.605 (m, 1H), 3.357 (s, 3H), 3.332 (m, 1H), 2.882 (m, 2H), 2.002 (m, 1H), 1.815 (m, 1H), 1.504 (s, 3H); 31P NMR (D2O, 121 MHz) 6.396; HRMS (FAB) m/z calcd for C13H20N6O8P (M+H)+ 419.1080, found 419.1103.

Provenance & Evidence