Ethyl Acetate → HCID 86644269, compound

Participants

Reaction Steps

Benzophenone hydrazone (500 mg, 2.5 mmol) in DCM (5 mL) was added dropwise over 15 min to a solution of p-nitrobenzyl chloroformate (600 mg, 3 mmol) in DCM (5 mL) at 0° C. The reaction mixture was stirred at room temperature under argon for an additional 1.5 h, until TLC, [(2:1 Hex:EtOAc), Rf (benzophenone hydrazone): 0.45 and Rf (3i): 0.7] indicated complete consumption of the starting material. To this mixture was added dropwise DIPEA (400 μL, 4.6 mmol) and the suspension was stirred for an additional 3 h at room temperature, (22° C.) under argon. The reaction mixture was diluted in DCM (60 mL) and extracted several times with NaHCO3 (8×30 mL). The organic phase was dried over MgSO4, concentrated in-vacuo and purified by flash chromatography using 2:1 Hexane:EtOAc [Rf (5i): 0.25] to yield a white solid (0.5 g, 60%). 1H NMR (CDCl3) δ: 1.19 (t, J=7 Hz, 3H), 4.02 (d, J=5.6 Hz, 2H), 4.13 (q, J=7 Hz, 2H), 6.78 (t, J=5.5 Hz, 1H), 7.1-7.4 (m, 10H), 7.61 (s, 1H); 13C NMR (CDCl3) δ: 13.8, 41.4, 61.0, 126.8, 127.8, 127.9, 128.1, 129.0, 129.1, 129.36, 129.43, 129.5, 131.4, 136.5, 148.2, 151.0, 154.9, 170.0; LCMS (ESI) Calcd. for C18H19N3O3, M+: 325.4. Found (M+H)+326.

Provenance & Evidence