Cyclopentanecarbonyl chloride → HCID 18172590, compound

Temperature

-78 °C

To a solution of rac-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (185 mg, 0.64 mmol) in tetrahydrofuran (15 mL), previously cooled to −78° C., was added slowly a 1.0 M solution of lithium bis(trimethylsilyl)amide (1.3 mL, 1.3 mmol). The solution was stirred for 15 min at −78° C., then cyclopentanecarbonyl chloride (0.08 mL, 0.64 mmol) was dropwise added. The reaction mixture was stirred for an additional 60 min at −78° C. before it was quenched by the addition of a saturated ammonium chloride solution (10 mL). The mixture was then extracted with ethyl acetate (3×10 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) to afford 3-cyclopentyl-2-(3,4-dichloro-phenyl)-3-oxo-N-thiazol-2-yl-propionamide (98 mg, 40% yield) as a yellow-orange solid: EI-HRMS m/e calcd for C17H16N2O2SCl2 (M+) 382.0309, found 382.0309.

1. stirringThe reaction mixture was stirred for an additional 60 min at −78° C. before it
2. customwas quenched by the addition of a saturated ammonium chloride solution (10 mL)
3. extractionThe mixture was then extracted with ethyl acetate (3×10 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate)

ORD record

ord-88f6f381b24d4a83bc0c342b7cdc893e

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608218B2