Uses
(5S)?-?5-?Benzyl-?2,?2,?3-?trimethyl-?4-?imidazolidinone acts as a reagent for the synthetic preparation of N-fluoro(methylcyclopropyloxycarbonylpiperidyl)ethyl trifluorophenylacetamide and its GPR119 receptor agonistic activity and SAR
Synthesis
General procedure for the synthesis of (S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one from (S)-2-amino-N-methyl-3-phenylpropanamide and acetone: recrystallized (S)-2-amino-N-methyl-3-phenylpropanamide (1 eq.), acetone (2 eq.) and ytterbium trifluoromethanesulfonate (0.01 eq.) were refluxed in chloroform (10 mL/mmol (S)-2-Amino-N-methyl-3-phenylpropanamide) were refluxed for 8 hours. Upon completion of the reaction, the reaction mixture was allowed to cool to room temperature and the solvent was subsequently removed by evaporation under reduced pressure. Finally, the crude product was purified by column chromatography to afford the target compound (S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one.
References
[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 133 - 141
[2] Chemistry - A European Journal, 2015, vol. 21, # 28, p. 10031 - 10038
[3] Tetrahedron, 2011, vol. 67, # 23, p. 4263 - 4267
[4] Helvetica Chimica Acta, 2014, vol. 97, # 6, p. 751 - 796
[5] Journal of the Chemical Society, Chemical Communications, 1990, # 19, p. 1321 - 1322
