Methyl 2-acetamidoacrylate

Last updated
Methyl 2-acetamidoacrylate
AcetamidoacrylateMe ester.png
Names
Preferred IUPAC name
Methyl 2-acetamidoprop-2-enoate
Other names
Methyl 2-(acetylamino)propenoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.107.415 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 609-121-9
PubChem CID
UNII
  • InChI=1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
    Key: SMWNFFKPVLVOQQ-UHFFFAOYSA-N
  • CC(=O)NC(=C)C(=O)OC
Properties
C6H9NO3
Molar mass 143.142 g·mol−1
Appearancewhite solid
Melting point 75–76 °C (167–169 °F; 348–349 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methyl 2-acetamidoacrylate is the organic compound with the formula CH2=C(NHC(O)CH3)CO2CH3. It is the methyl ester of an N-acetyl acrylic 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]

N-Acetamidoacrylic acid (registry number 5429-56-1) is the carboxylic acid parent of methyl 2-acetamidoacrylate. The free acid is a popular substrate for asymmetric hydrogenation. [3]

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ Fryzuk, M. D.; Bosnich, B. (1977). "Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation". Journal of the American Chemical Society. 99 (19): 6262–6267. Bibcode:1977JAChS..99.6262F. doi:10.1021/ja00461a014. PMID   893889.
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