Benzylamine → HCID 19029222, compound

Participants

Reaction Steps

4-Methylmorpholine (0.71 g, 6.99 mmol) was added to a suspension of 2-acetamido-2-vinylacetic acid (1.00 g, 6.99 mmol) in THF (325 mL), and the mixture was stirred at room temperature (30 min). The reaction was cooled to -10° to -15° C. and then isobutylchloroformate (1.24 g, 9.08 mmol) was then added dropwise. After stirring (10 min), a solution of benzylamine (0.75 g, 6.99 mmol) in THF (25 mL) was added (15 min). The reaction mixture was allowed to warm to 0° C. The insoluble material was filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on SiO2 gel using 3% MeOH/CHCl3 as the eluant to give 1.00 g (62%) of the desired product: mp 136°-138° C. (recrystallized from EtOAc); Rf 0.24 (3% MeOH/CHCl3); 1H NMR (DMSO-d6) δ 1.88 (s, C(O)CH3), 4.27 (d, J=5.6 Hz, CH2), 4.89-4.94 (dd, J=6.4, 7.8 Hz, α-CH), 5.13-5.30 (m, --CH=CH2), 5.81-5.93 (m, --CH=CH2), 7.20-7.33 (m, 5 PhH), 8.27 (c, J=7.8 Hz, NH), 8.58 (t, J=5.6 Hz, NH); 13C NMR (DMSO-d6) 22.47 (C(O)CH3), 42.05 (CH2), 55.24 (α-CH), 116.44 (CH=CH2), 126.74 (C4'), 127.05 (2C2' or 2C3'), 128.24 (2C2' or 2C3'), 134.76 (CH=CH2), 139.25 (C1'), 168.78 (C(O)CH3), 168.99 (C(O)NH) ppm.

Provenance & Evidence