Carbon Dioxide → HCID 19029178, compound

Participants

Reaction Steps

Employing the mixed carbonic anhydride coupling procedure with 18 (2.40 g, 12.2 mmol), 4-methylmorpholine (1.23 g, 12.2 mmol), isobutylchloroformate (1.83 g, 13.4 mmol), and benzylamine (1.43 g, 12.7 mmol) gave 4 (1.50 g, 43%) as a thick oil: Rf 0.29 (2% MeOH/CHCl3); 1H NMR (CDCl3) δ 1.94 (s, CH3), 1.98 (s, C(O)CH3), 4.40 (d, J=5.6 Hz, CH2), 6.20 (br s, NH), 6.34-6.37 (m, C3H, C4H), 7.05-7.36 (m, NH, C5H, 5 PhH); 13C NMR (CDCl3) 22.31 (C(O)CH3), 23.81 (CH3), 43.77 (CH2), 58.50 (C(CH3)), 107.94 (C4), 110.67 (C3), 126.99 (2C2 ' or 2C3 '), 127.41 (C4 '), 128.60 (2C2 ' or 2C3 '), 137.52 (C1 '), 142.38 (C5), 152.94 (C2), 169.03 (C(O)NH), 171.16 (COCH3) ppm; mass spectrum, m/e (relative intensity) 287 (M+ +1, 4), 228 (4), 153 (99), 152 (96), 138 (15), 111 (63), 110 (100), 91 (75); Mr (EI) 286.13074 (calcd for C16H18N2O3, 286.13174).

Provenance & Evidence