Methyl 2-acetamidoacrylate is the organic compound with the formula CH2=C(NHC(O)CH3)CO2CH3. It is the methyl ester of an N-acetylacrylic acid, which in turn is a derivative of the unstable compound dehydroalanine. Acetylation of the amine in the latter compound prevents tautomerization. It is a white solid.
The compound can be prepared from methyl 2-acetamidopropionate (CH3CH(NHC(O)CH3)CO2CH3), i.e. the methyl ester of N-acetylalanine.[1] Methyl 2-acetamidoacrylate undergoes Michael reactions, e.g. by thiolates.[2]
References
- ^ Kolar, A. J.; Olsen, R. K. (1977). "A Convenient, Large-Scale Preparation of 2-Acetamidoacrylic Acid and Its Methyl Ester". Synthesis. 1977 (7): 457–9. doi:10.1055/s-1977-24439. S2CID 96352441.
- ^ Petracca, R.; Bowen, K. A.; McSweeney, L.; O’Flaherty, S.; Genna, V.; Twamley, B.; Devocelle, M.; Scanlan, E. M. (2019). "Chemoselective Synthesis of N-Terminal Cysteinyl Thioesters via β,γ-C,S Thiol-Michael Addition". Organic Letters. 21 (9): 3281–3285. doi:10.1021/acs.orglett.9b01013. PMID 31017793. S2CID 131775844.