Electric Literature of 5238-56-2,Some common heterocyclic compound, 5238-56-2, name is N-(2-Hydroxyethyl)methacrylamide, molecular formula is C6H11NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
N-(2-hydroxyethyl) methacrylamide (3.30 mL, 25.6 mmol, 1.0 eq), triethylamine (7.15 mL, 51.2 mmol, 2.0 eq) and 50 mL DCM were added into a 250 mL flask. After the reaction system was cooled down by an ice bath, butyric anhydride (5.00 mL, 30.7 mmol, 1.2 eq) was added dropwise under the protection of nitrogen. The system was allowed to react overnight. The reaction mixture was filtered and washed by NH4CI solution, NaHCCb solution, and water. After dried by anhydrous MgSC , the organic layer was concentrated by rotary evaporation and purified on a silica column using DCM/MeOH. The product N- butanoyloxyethyl methacrylamide (3) was obtained as pale yellow oil (4.56 g, 89.6%) and analyzed by 1H-NMR (500 MHz, CDCb) deltaEta ppm 0.95 (t, 3H, CH2CH2-CH3), 1.66 (m, 2H, CH2-CH2), 1.97 (s, 3H, C(CH2)-CH3), 2.32 (t, 2H, CO-CH2), 3.59 (dt, 2H, NH-CH2), 4.23 (t, 2H, O-CH2), 5.35 (s, IH, CCH2), 5.71 (s, IH, CCH2), 6.19 (br s, IH, NH). This example demonstrates the feasibility of attaching pharmaceutically-active small molecules to a monomeric unit of the block copolymer. Additional SCFAs can be attached to the monomeric unit in a similar manner.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(2-Hydroxyethyl)methacrylamide, its application will become more common.
Reference:
Patent; THE UNIVERSITY OF CHICAGO; HUBBELL, Jeffrey A.; WANG, Ruyi; WILSON, D. Scott; NAGLER, Cathryn R.; PLUNKETT, Catherine; (90 pag.)WO2018/195067; (2018); A1;,
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