4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Chemical Properties

Boiling point:

357.8±31.0 °C(Predicted)

Density 

1.320

storage temp. 

2-8°C

pka

10.82±0.40(Predicted)

Appearance

Colorless to light yellow Liquid

4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 2-oxoxoxazolidine-4-carboxylate from tritiated gas and L-serine methyl ester hydrochloride: a THF solution of tritiated gas (60 mL, 11.4 g, 38.58 mmol, 1.0 eq.) was slowly added to a tetrahydrofuran (THF, 90 mL) suspension of L-serine methyl ester hydrochloride (6 g, 38.58 mmol). The reaction mixture was heated to reflux for 4 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by rapid chromatography on silica gel (eluent ratio: ethyl acetate/hexane = 3:1) to afford the target product methyl 2-oxoxoxazolidine-4-carboxylate (4.38 g, 78% yield) as a white solid.

References

[1] Chemistry - A European Journal, 2007, vol. 13, # 1, p. 135 - 149
[2] Recueil des Travaux Chimiques des Pays-Bas, 1995, vol. 114, # 4-5, p. 163 - 170
[3] Tetrahedron Letters, 1995, vol. 36, # 49, p. 8961 - 8964
[4] Journal of the American Chemical Society, 1999, vol. 121, # 33, p. 7509 - 7516
[5] Organic Letters, 2011, vol. 13, # 22, p. 6010 - 6013