Carbon Dioxide → HCID 14978602, compound

Participants

Reaction Steps

Using racemic 19 (3.00 g, 16.39 mmol), 4-methylmorpholine (1.66 g, 16.39 mmol), isobutylchloroformate (2.24 g, 16.39 mmol), and 3-aminomethylpyridine (1.77 g, 16.39 mmol) in the mixed carbonic anhydride protocol gave 3.35 g (75%) of 7: mp 172°-174° C. (recrystallized from EtOAc); Rf 0.27 (8% MeOH/CHCl3); IR (KBr) 3400, 3300, 1640, 1540, 1420, 1360, 820, 740 cm-1 ; 1H NMR (DMSO-d6) δ 1.89 (s, C(O)CH3), 4.32 (d, J=5.8 Hz, CH2), 5.55 (d, J=7.9 Hz, CH), 6.28-6.29 (m, C3H), 6.41-6.43 (m, C4H), 7.32 (dd, J=4.8, 7.7 Hz, C5 'H), 7.58-7.62 (m, C4 'H, C5H), 8.44 (br s, C2 'H, C6 'H), 8.62 (d, J=7.9 Hz, NH), 8.81 (t, J=5.8 Hz, NH); 13C NMR (DMSO-d6) 22.31 (C(O)CH3), 39.98 (CH2), 50.94 (CH), 107.67 (C4), 110.54 (C3), 123.38 (C5 '), 134.57 (C3 '), 134.83 (C4 '), 142.64 (C5), 148.06 (C6 '), 148.55 (C2 '), 150.94 (C2), 168.19 (C(O)NH), 169.26 (C(O)CH3) ppm; mass spectrum (FD) 274 (M+ +1). Anal. (C14H15N3O3) C, H, N. ##STR41##

Provenance & Evidence