Dimethylformamide → HCID 86658642, compound

Participants

Reaction Steps

Lithium 2-(3-amino-4-formylphenoxy)acetate (44.2 mg) and HBTU (79.6 mg) were put in a 20 mL glass vial and dry DMF (5 mL) was added. The resulting slurry was stirred at ambient temperature, which turned homogeneous within 10 minutes. After 15 min DIEA (50 μL) and 4′-nitrobenzylamine HCl (37.7 mg) were added to the reaction mixture, and the reaction was stirred at ambient temperature. After 30 minutes LC-MS analysis revealed a complete reaction. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed successively with dil. aq. citric acid, sat. aq. NaHCO3, and sat. aq. NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure, affording the title compound as a tan solid. MS (ESI+): m/z 330.10 (MH+). H-NMR (400 MHz, DMSO-d6): 4.463 (2H, d, J=6.0 Hz), 4.597 (2H, s), 6.246 (1H, d, J=2.4 hz), 6.308 (1H, dd, J=2.4 Hz, 8.8 Hz), 7.235 (1H, br.s), 7.465 (1H, d, 8.8 Hz), 7.518 (2H, d, J=8.8 Hz), 8.173 (2H, d, J=8.8 Hz), 8.821 (1H, t, J=6.2 Hz), 9.657 (1H, s). C-NMR (400 MHz, DMSO-d6): 41.415, 66.627, 98.724, 104.297, 113.217, 123.267, 128.056, 137.581, 146.303, 147.287, 152.698, 162.872, 167.526, 191.685.

Provenance & Evidence