(R)-Methyl 2-amino-3-phenylpropanoate → 3-Azido-3-deoxythymidine 5-methoxy-D-phenylalaninylphosphoramidate

Participants

Reaction Steps

Compound 40 (340 mg, 0.785 mmol) and D-phenylalanine methyl ester (HCl salt, 339 mg, 1.57 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 (282 mg, 68%) as a white solid. 1H NMR (D2O, 300 MHz) 7.415 (s, 1H), 7.1580-6.998 (m, 5H), 5.995 (t, J=6.8 Hz, 1H), 4.118 (m, 1H), 3.808 (m, 1H), 3.738 (m, 1H), 3.661 (m, 1H), 3.467 (m, 1H), 3.403 (s, 3H), 2.754 (m, 2H), 2.212 (m, 2H), 1.679 (s, 3H); 31P NMR (D2O, 121 MHz) 6.204; HRMS (FAB) m/z calcd for C13H20N6O8P (M+H)+ 419.1080, found 419.1103.

Provenance & Evidence