2-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl ester → HCID 22880304, compound

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Reaction Steps

Compound 9 (1.5 g) was dissolved in water/methanol (1:1, 10 mL) to which triethylamine was added to obtain pH 10. N-acryloyloxy succinimide (2.0 g) was added and the mixture was stirred for 2 hr. After TLC analysis indicated the complete disappearance of starting material 9, the volatiles were removed from the reaction mixture. The residue was chromatographed on a silica gel column using 20% methanol in dichloromethane. The appropriate fractions were pooled and solvent was removed to give the derivative 10 as a white foam (1.1g). 13N NMR (D2O): δ, 1.62-1.95, mm, 6H; 2.64-2.80, m, 2H; 3.05-3.14, m, 2H; 3.28-3.35, m, 1H; 3.68-3.72, dd, 1H 2H; 4.24-4.29, m, 1H; 4.38-4.41, m, 2H; 5.82-5.86,dd, 2H , acryloyl CH2; 6.26-6.36,m, 1H, acryloyl CH: 13C NMR (D2O): 176.92, 175.14, 168.12, 129.42, 78.76, 74.44, 71.47, 66.38, 66.41, 65.70, 60.72, 38.21, 30.11, 27.62, 24.49, 22.31.

Provenance & Evidence