With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.
A solution of methyl fumarate (8) (2.66 g, 20.4 mmol) and pivaloyl chloride (2.70 g, 2.76 mL, 22.5 mmol) in THF (40 mL) was cooled to ?20 ¡ãC.? Triethylamine (4.13 g, 5.68 mL, 40.8 mmol) was added dropwise, and the mixture was stirred 1.5 h at ?20 ¡ãC.? The cooling bath was removed, and the solution was allowed to warm to room temperature.? Solid LiCl (0.953 g, 22.5 mmol) and (R)-phenyl-oxazolidone 9 (5.00 g, 30.6 mmol) were added portionwise, and the reaction was stirred 12 h. H2O (10 mL) and ethyl acetate (50 mL) were added. The layers were separated, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL).? The combined organic layers were washed with 1 M HCl (1 x 25 mL), saturated Na2CO3 (2 x 50 mL), saturated brine (1 x 50 mL), dried (Na2SO4), and concentrated under reduced pressure.? The crude product was purified by flash chromatography, eluting with hexanes/ethyl acetate (3:1) to provide 4.38 g (78percent) of the chiral methyl fumarate 7 as a white solid: mp 92-94 ¡ãC; 1H NMR (400 MHz) delta 8.17 (d, J = 15.7 Hz, 1 H), 7.43 (comp, 5 H), 6.87 (d, J = 15.7, 1 H), 5.50 (dd, J = 4.0, 8.9 Hz, 1 H), 4.76 (t, J = 8.9 Hz, 1 H), 4.36 (dd, J = 4.0, 8.9 Hz, 1 H), 3.81 (s, 3 H); 13C NMR (100 MHz) delta 165.1, 163.1, 153.2, 138.2, 133.8, 132.2, 129.1, 128.8, 125.9, 70.2, 57.7, 52.2; IR (neat) 1780, 1727, 1690, 1387, 1341, 1306, 1279, 1196 cm-1; mass spectrum (CI) m/z 275.0869 [C14H13NO5 (M+1) requires 275.0794]., 90319-52-1
The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Hethcox, J. Caleb; Shanahan, Charles S.; Martin, Stephen F.; Tetrahedron Letters; vol. 54; 16; (2013); p. 2074 – 2076;,
Oxazolidine – Wikipedia
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