反应详情

under an N2 atmosphere, 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide (0.578 g, 1.46 mmol) was dissolved in DMF (7.00 ml). Dess-Martin periodinane (0.745 g, 1.76 mmol) was added and the reaction was stirred at room temperature for 3 hours. The reaction was diluted with ethyl acetate and a saturated aqueous solution of sodium bisulfate. The layers were separated and the organic layer was washed with water and brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and hexanes. The resulting solid was collected by filtration. The solid was suspended in pyridine (8.00 ml) and POCl3 (4.00 ml). The reaction was heated to 70° C. for 3 hours. The reaction was poured into a cooled 5% NaHCO3 solution and stirred vigorously for 15 minutes. The mixture was then extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography eluting with 25% to 50% ethyl acetate in hexanes. The resulting solid was triturated with ethyl acetate/hexanes and collected by filtration to afford 2-chloro-N-(4-(5-phenyloxazol-2-yl)phenyl)benzamide (0.920 g, 16.8%). ESI m/z=375.0 (M+H+).

1. customThe layers were separated
2. washthe organic layer was washed with water and brine
3. dry with materialThe organic layer was dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was triturated with ethyl acetate and hexanes
7. filtrationThe resulting solid was collected by filtration
8. temperatureThe reaction was heated to 70° C. for 3 hours
9. additionThe reaction was poured into a cooled 5% NaHCO3 solution
10. stirringstirred vigorously for 15 minutes
11. extractionThe mixture was then extracted with ethyl acetate
12. dry with materialThe organic layer was dried (Na2SO4)
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customThe crude residue was purified by column chromatography
16. washeluting with 25% to 50% ethyl acetate in hexanes
17. customThe resulting solid was triturated with ethyl acetate/hexanes
18. filtrationcollected by filtration