Benzylamine → HCID 19029179, compound

Participants

Reaction Steps

4-Methylmorpholine (0.55 g, 5.40 mmol) was added to a cooled (-10° to -15° C.) THF solution (60 mL) of 2-acetamido-4-pentenoic acid (0.81 g, 5.18 mmol), and then isobutylchloroformate (0.75 g. 5.70 mmol) was added leading to the precipitation of a white solid. After 2 min, a solution of benzylamine (0.61 g, 5.70 mmol) in THF (10 mL) was slowly added at -10° to -15° C. The reaction was allowed to warm (5 min) at room temperature and the insoluble salts were removed by filteration, and the filtrate was evaporated to dryness. The residue was triturated with EtOAc (10 mL), and the remaining white solid was filtered to give 0.81 g (64%) of the desired product: mp 118°-120° C. (recrystallized from ethyl acetate/cyclohexane); Rf 0.36 (4% MeOH/CHCl3); IR (KBr) 3200 (br), 3040, 2900, 1650 (br), 1540 (br), 1350, 750, 700 cm-1 ; 1H NMR (DMSO-d6) δ 1.83 (s, C(O)CH3), 2.22-2.49 (m, CH2CH=CH2), 4.26 (d, J=5.3 Hz, CH2Ph), 4.25-4.33 (m, CH), 4.99-5.09 (m, CH2CH=CH2), 5.65-5.77 (m, CH2CH=CH2), 7.21-7.29 (m, 5 PhH), 8.05 (d, J=7.6 Hz, NH), 8.46 (br s, NH); 13C NMR (DMSO-d6) 22.41 (C(O)CH3), 36.24 (CH2CH=CH2), 41.91 (CH2Ph), 52.20 (CH), 117.15 (CH2CH=CH2), 126.54 (C4'), 126.99 (2C2' or 2C3'), 128.04 (2C2' or 2C3'), 139.25 (C1'), 134.25 (CH2CH=CH2), 169.02 (C(O)CH3), 170.96 (C(O)NH) ppm; mass spectrum, m/e (relative intensity) 246 (M+, 4), 205 (4), 163 (15), 140 (8), 106 (33), 91 (77), 70 (100).

Provenance & Evidence