반응 #983293

반응 방정식

1,1′-carbonyldiimidazole

3-fluoro-4-morpholinoaniline

ethyl 2(R)-epoxypropanoate

lithium triflate

→

title compound

ethyl (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate

용매

acetonitrile

반응 조건

후처리

1. 1
   기타Solvent and excess epoxide is removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe crude amino alcohol is redissolved in dry acetonitrile (40 mL)
3. 3
   기타the solvent is removed under reduced pressure
4. 4
   기타The residue is partitioned between ethyl acetate (70 mL) and 3% aqueous citric acid (100 mL)
5. 5
   기타the layers are separated
6. 6
   세척the organic phase is washed with 3% aqueous citric acid (3×100 mL), water and saline
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The product mixture is then purified by silica gel chromatography
10. 10
    세척eluting with ethanol/methylene chloride (2/98)
11. 11
    농축concentrated

실험 절차

A solution of 3-fluoro-4-morpholinoaniline (J. Med. Chem. 1996, 39(3), 673-679, 0.796 g, 4.0 mmol), ethyl 2(R)-epoxypropanoate (0.696 g, 6.0 mmol) and lithium triflate (0.97 g, 6.2 mmol) in acetonitrile (12 mL) is stirred at 50-60° C. overnight. Solvent and excess epoxide is removed under reduced pressure, and the crude amino alcohol is redissolved in dry acetonitrile (40 mL) and 1,1′-carbonyldiimidazole (1.46 g, 9.0 mmol) is added. The mixture is stirred at ambient temperature overnight, and then the solvent is removed under reduced pressure. The residue is partitioned between ethyl acetate (70 mL) and 3% aqueous citric acid (100 mL), the layers are separated, and the organic phase is washed with 3% aqueous citric acid (3×100 mL), water and saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product mixture is then purified by silica gel chromatography, eluting with ethanol/methylene chloride (2/98), and the appropriate fractions are pooled and concentrated to give the title compound, MS (ESI+) for C16H19N2O5F m/z 339 (M+H)+.

출처