反应详情

A solution of crude 2-(3,4-dichloro-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-N-thiazol-2-yl-propionamide (768.5 mg, 1.74 mmol) in tetrahydrofuran (8.7 mL) and a 5% aqueous hydrochloric acid solution (3.9 mL) was stirred at 25° C. for 64 h. The resulting reaction solution was concentrated in vacuo to remove tetrahydrofuran and then diluted with ethyl acetate (100 mL). The organic layer was washed with a 1% aqueous hydrochloric acid solution (50 mL), water (50 mL) and a saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50% ethyl acetate/hexanes) afforded 2-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide (481.9 mg, 47% over 2 steps) as a white solid: mp 146–148° C.; (ES)+-HRMS m/e calcd for C17H16Cl2N2O2S (M+H)+ 383.0383 found 383.0385.

1. customThe resulting reaction solution
2. concentrationwas concentrated in vacuo
3. customto remove tetrahydrofuran
4. additiondiluted with ethyl acetate (100 mL)
5. washThe organic layer was washed with a 1% aqueous hydrochloric acid solution (50 mL), water (50 mL)
6. dry with materiala saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo