Sodium Carbonate → HCID 18391586, compound

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.

1. filtrationThe resulting blue precipitate was filtered
2. washwashed with H2O, acetone, ether
3. customAfter air-drying
4. customthe violet-blue solid (26) was purified by ion exchange
5. additionca. 40 mL of DOWEX® 50WX8-400 resin was treated with 1 M NH4OH (100 mL)
6. additionthe suspension was poured into a column
7. washwashed with conc. NH4OH
8. dissolutionThe copper complex (26) was dissolved in conc. NH4OH (2 mL)
9. washeluted with ca. 500 mL of conc. NH4OH
10. customThe solution was evaporated in vacuo
11. customdried under high vac

ORD record

ord-dded77ef42b14461a38839a35685bd74

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394357B2