Hydrochloric Acid → HCID 15928542, compound

Participants

Reaction Conditions

Reaction Steps

A thick-walled reaction flask with a screw top was charged sequentially with (S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid (Chem-Impex Int'l Inc., 5.0 g, 12 mmol), 1,2-dimethoxyethane (5.0 mL), formaldehyde (37% wt. in H2O, 4.5 mL, 60 mmol), and conc. HCl (60.2 mL, 1981 mmol). The resulting tan slurry was sealed with a screw top and heated to 72° C. slowly over 30 min and then maintained at 72° C. for 12 h. The resulting brown reaction slurry was then cooled to 0° C., filtered while cold, and washed with small amounts of 1,2-dimethoxyethane to give the title compound (2.42 g, 5.45 mmol, 47%) as a white solid. 1H NMR (DMSO-d6) δ 9.93 (br s, 1H), 9.69 (br s, 1H), 7.75 (s, 1H), 4.34 (d, J=7.7 Hz, 1H), 4.21-3.94 (m, 2H), 3.93-3.47 (m, 1H), 3.33-3.16 (m, 1H), 3.15-2.97 (m, 1H); MS (ESI+) m/z 445.9 (M+H)+.

Provenance & Evidence