Hydrochloric Acid → HCID 67158850, compound

Temperature

0 °C

1.15 g (5.69 mmol) of Na2B4O7 was dissolved in 30 ml of water. The solution was degassed with Ar for 30 minutes, after which 0.592 g (3.0 mmol) of L-DOPA was added and stirred for 15 minutes. 0.317 g (3.0 mmol) of Na2CO3 was then added, the solution was cooled to 0° C., and 0.3 ml (3.0 mmol) of methacryloyl chloride was slowly added with stirring. The pH of the solution was maintained above 9 with Na2CO3 during the reaction. After stirring for 1 hour at room temperature, the solution was acidified to pH of 2 with concentrated HCl. The mixture was extracted with ethyl acetate three times. After washing with 0.1 N HCl and drying over anhydrous MgSO4, the solvent was removed in vacuo to yield crude light brown solid. The product was further purified by elution from a silica gel column with dichloromethane (DCM) and methanol (95:5). After evaporating the solvent, a white, sticky solid was obtained with a product yield of 35%. 1H NMR (500 MHz, acetone-d6): ÿ 7.1 d(1H, —NH—); 6.6-6.8 (3H, C6H3(OH)2—); 5.68 s (1H, CHH═); 5.632 s (unknown peak); 5.33 s (1H, CHH═); 4.67 m (1H, —CH—); 2.93-3.1 m (2H, CH2—); 1.877 s (3H, —CH3).

1. customThe solution was degassed with Ar for 30 minutes
2. stirringwith stirring
3. stirringAfter stirring for 1 hour at room temperature
4. extractionThe mixture was extracted with ethyl acetate three times
5. washAfter washing with 0.1 N HCl
6. dry with materialdrying over anhydrous MgSO4
7. customthe solvent was removed in vacuo
8. customto yield crude light brown solid
9. customThe product was further purified by elution from a silica gel column with dichloromethane (DCM) and methanol (95:5)
10. customAfter evaporating the solvent

ORD record

ord-02a7da37ea3644a2981e4ac48c9646f9

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815793B2