Sodium Carbonate → HCID 18391586, compound

Participants

Reaction Steps

Methacryloyl chloride (4.8 mL, 50 mmol) was slowly added, via syringe, to a cooled (0° C.) solution of lysine monohydrochloride (8.0 g, 43.6 mmol), CuSO4.5H2O (5.46 g, 21.8 mmol), NaOH (3.6 g, 90 mmol), and Na2CO3 (4.6 g, 43.6 mmol) in H2O (80 mL). The reaction was stirred at RT for 2 h. The resulting blue precipitate was filtered and washed with H2O, acetone, ether, then H2O again. After air-drying, the violet-blue solid (26) was purified by ion exchange: ca. 40 mL of DOWEX® 50WX8-400 resin was treated with 1 M NH4OH (100 mL), and the suspension was poured into a column and washed with conc. NH4OH. The copper complex (26) was dissolved in conc. NH4OH (2 mL), loaded onto the column, and eluted with ca. 500 mL of conc. NH4OH. The solution was evaporated in vacuo, and dried under high vac. to yield pure 27 as a white solid (5.5 g, 60%). 1H NMR (250 MHz, D2O) δ: 1.53 (m, 2H), 1.67 (m, 2H), 1.98 (m, 2H), 2.02 (s, 3H), 3.37 (t, J=6.5, 2H), 3.83, (t, J=6.0, 1H), 5.53, (s, 1H), 5.77 (s, 1H); 13C NMR (69.3 MHz, D2O) δ: 17.75, 21.85, 28.12, 30.14, 39.14, 54.71, 120.82, 139.22, 171.93, 174.79. See Makromol. Chem. 1980, 181, 2183-2197.

Provenance & Evidence