Chlorotrimethylsilane → HCID 178517977, compound

Temperature

-78 °C

A dry 100 mL round-bottomed flask was charged with 5-cyclopentyl-2-(2-fluorophenylamino)thiazol-4(5H)-one (0.200 g, 0.717 mmol) and 6.0 mL of THF. This solution was cooled to −78° C., and LDA (2.0 M in THF/heptane/ethyl benzene, 1.43 mL, 2.86 mmol) was added. The resulting brown solution was allowed to stir at that temperature for 1 h, then TMSCl (0.623 g, 0.725 mL, 5.74 mmol) was added. The solution was warmed to room temperature and allowed to stir for an additional 1 h. The solution was concentrated in vacuo to remove the volatiles and then redissolved in 10 mL of CH3CN. Selectfluor (0.508 g, 1.43 mmol) was added at room temperature, and the resulting solution was stirred for 2 h. The reaction was quenched with saturated aqueous NaHCO3, and the resulting mixture was thoroughly extracted with CH2Cl2. This combined organic extracts were dried and concentrated in vacuo to give an oil which was purified by column chromatography (100% to 70% hexanes/30% ethyl acetate) to give the title compound as a colorless oil. Mass Spec (M+H)+; 297.1.

1. temperatureThe solution was warmed to room temperature
2. stirringto stir for an additional 1 h
3. concentrationThe solution was concentrated in vacuo
4. customto remove the volatiles
5. dissolutionredissolved in 10 mL of CH3CN
6. stirringthe resulting solution was stirred for 2 h
7. customThe reaction was quenched with saturated aqueous NaHCO3
8. extractionthe resulting mixture was thoroughly extracted with CH2Cl2
9. customThis combined organic extracts were dried
10. concentrationconcentrated in vacuo
11. customto give an oil which
12. customwas purified by column chromatography (100% to 70% hexanes/30% ethyl acetate)

ORD record

ord-a76c341eaa364f629cf0518846328717

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253196B2