Butylamine → Clevudine

Participants

Reaction Steps

A solution of 23 (47 mg, 0.1 mmol) and n-butylamine (0.74 g, 1.0 mL, 10 mmol) in methanol (2 mL) was heated at reflux for 3 hours. The solution was evaporated to dryness and triturated with ethyl ether to afford a solid that was filtered, washed with ether and dried to afford 24 (20 mg, 0.077 mmol, 77% as a white solid: mp 188° C. (lit. value: mp 185-187° C., 184-185° C., 187-188° C. for the D-isomer); [α]D20=−93 (c 0.25 MeOH); (lit. value: [α]D20=−111 (c 0.23 MeOH), [α]D20=−122 (c0.023 MeOH)); 1H-NMR (DMSO-d6) δ 11.0 (1H, bs, N—H, 7.58 (1H, s, C—H thymine), 6.09 (1H, dd, J=4.2 and J=15.6, H-1), 5.85 (1H, bs, OH), 5.10 (1H, bs, OH), 5.02 (1H, dt, J−4.0, J−3.8 and J−52.8, H-2), 4.22 (1H, dt, J−3.8, J−4.0 and J=20.3, H-3), 3.76 (1H, q, J=4.0 and J−9.5, H-4), 3.69-3.57 (2H, m, H-5 and H-5′), 1.77 (3H, s, Thymine CH3).

Provenance & Evidence