1,2-Dichloroethane → HCID 68666149, compound

Participants

Reaction Steps

A stirred solution of said benzoic acid (0.5 g, 1.87 mmol) in DMF at 0° C., was treated sequentially with EDC (0.47 g, 2.1 mmol, 1.2 eq), HOBt (0.29 g, 2.1 mmol, 1.2 eq), DIPEA (0.8 g, 4.2 mmol, 2.5 eq) and serine methyl ester hydrochloride (0.33 g, 2.1 mmol, 1.2 eq), stirred overnight at room temperature and evaporated under reduced pressure. The resultant residue was partitioned between EtOAc and water. The phases were separated. The organic phase was washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. This residue was purified by column chromatography (silica, CHCl3:MeOH 4%) to afford the title product in 58% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 8.52 (d, J=8 Hz, 1H), 7.95 (s, 1H), 7.84 (d, J=8 Hz, 2H), 7.84 (d, J=8 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 2H), 7.14-7.23 (m, 2H), 5.05 (t, J=7.2 Hz, 1H), 4.53 (m, 1H), 4.37 (s, 2H), 3.77 (t, J=7.2 Hz, 1H), 3.70 (s, 3H), 3.64 (s, 3H). LCMS (ESI+) 367 (MH+).

Provenance & Evidence