tert-Butyl bromoacetate → HCID 68460850, compound

The compound of Example 145 (280 mg) was dissolved in tetrahydrofuran (12 mL) in an argon atmosphere. While the solution was kept at −78° C., 1 mol/L lithium bis(trimethylsilyl)amide/tetrahydrofuran solution (1.23 mL) was added and the mixture was stirred at −78° C. to room temperature for 30 min. t-butyl bromoacetate (181.6 μL) was then added at −78° C. and the mixture was stirred at room temperature for 7 hours. Subsequently, the reaction was terminated by adding a saturated aqueous solution of ammonium chloride and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=1:1) afforded the title compound as a green powder (237.1 mg).

1. customwas kept at −78° C.
2. additionwas then added at −78° C.
3. customSubsequently, the reaction was terminated
4. additionby adding a saturated aqueous solution of ammonium chloride
5. extractionthe mixture was extracted three times with ethyl acetate
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over sodium sulfate
8. customEvaporation of the solvent
9. customunder reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-25c3032b886f48baaf8ad5146b409311

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763617B2