L-Tryptophan, methyl ester → 3-Azido-3-deoxythymidine 5-methoxy-L-trytophanyl-phosphoramidate

Participants

Reaction Steps

Compound 40 (218 mg, 0.503 mmol) and tryptophan methyl ester (HCl salt, 258 mg, 1.01 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 (198 mg, 70%) as a white solid. 1H NMR (D2O, 300 MHz) 7.222 (d, J=7.9 Hz, 1H), 7.103 (d, J=8.1 Hz, 1H), 7.072 (s, 1H), 6.880 (s, 1H), 6.857 (t, J=7.7 Hz, 1H), 6.729 (t, J=7.5 Hz, 1H), 5.690 (t, J=6.6 Hz, 1H), 3.883 (m, 1H), 3.763 (m, 1H), 3.635 (m, 1H), 3.527 (m, 2H), 3.448 (s, 3H), 2.899 (m, 1H), 2.765 (m, 1H), 1.857 (m, 1H), 1.682 (m, 1H), 1.493 (s, 3H); 31P NMR (D2O, 121 MHz) 6.412; HRMS (FAB) m/z calcd for C13H20N6O8P (M+H)+ 419.1080, found 419.1103.

Provenance & Evidence