反应详情

4-[4-[(Hydroxyimino)methyl]-2-thiazolyl]-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine (i.e. the product of Example 2, Step C) (0.2 g, 0.5 mmol) was suspended in tetrahydrofuran (20 mL), and phenylacetylene (1.1 mL, 1 mmol) was added, followed by a slow dropwise addition of Clorox® bleach solution (6.15 wt. % sodium hypochlorite, 10 mL) over 1 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×0 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure to give an oil, which was purified by flash column chromatography on silica gel using 10% methanol in ethyl acetate as eluant to give 70 mg of the title product, a compound of present invention, as a clear yellow oil.

1. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with ethyl acetate (3×0 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customto give an oil, which
8. customwas purified by flash column chromatography on silica gel using 10% methanol in ethyl acetate as eluant