Water → HCID 18639108, compound

Participants

Reaction Steps

A mixture of 1-[2-deoxy-3-O-mesyl-5-O-methoxycarbonyl-β-D-threopentofuranosyl]-thymine (5.0 g, 13.2 mmoles) from Example A13 and sodium azide (1.07 g, 16.5 mmoles) in dimethylformamide (40 mL) was heated at 85°-90° C. for 4 h. The suspension was cooled to ambient temperature poured into 300 mL of water and the aqueous solution extracted with 3×100 mL portions of ethyl acetate. The combined organic extracts were washed with 2×100 mL portions of water and concentrated by rotary evaporation affording 3.88 g (90.2%) of 3'-azido-3'-deoxy-5'-O-(methoxycarbonyl)thymidine as a colorless oil: 1H NMR (CDCl3) δ1.91 (d, J=1.15 Hz, 3H, C-5-CH3), 2.30-2.49 (m, 2H, C-2'H), 3.83 (s, 3H, CO2CH3), 3.97-4.44 (m, 4H, C-3'H, C-4'H and C-5'H), 6.21 (t, J=6.26 Hz, 1H, C-1'H), 7.29 (q, J=1.15 Hz, 1H, C-6H) and 8.75 (broad, 1H, NH); 13C NMR (CDCl3) δ12.42, 37.57, 55.28, 60.04, 66.39, 81.56, 84.94, 111.38, 135.28, 150.45, 155.18 and 164.03; TLC, Rf =0.78, silica gel, CHCl3 :CH3OH/90:10.

Provenance & Evidence