N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → (E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-hydroxy-propyl]phenyl}-acryloylamino)-phenyl]carbamic acid tert-butyl ester

To a solution of (E)-[2-(3-{4-[1-(4-bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (1.6 g, 2.26 mmol) in THF (40 mL) was added tetrabutylammonium dihydrogen trifluoride (1.36 g, 4.52 mmol). This mixture was stirred at room temperature overnight and then evaporated to remove THF. The mixture was dissolved in water and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated. The crude product was purified by column chromatography (CH2Cl2:EtOAc=10:1) to get yellow solid product. MS: calc'd 594 (MH+), exp 594 (MH+).

1. customevaporated
2. customto remove THF
3. dissolutionThe mixture was dissolved in water
4. extractionextracted with ethyl acetate (3×30 mL)
5. washThe combined organic layer was washed with brine
6. dry with materialdried with Na2SO4
7. filtrationfiltered
8. customevaporated
9. customThe crude product was purified by column chromatography (CH2Cl2:EtOAc=10:1)
10. customto get yellow solid product

ORD 기록

ord-b32e868c6d2b43aea803d8f3db5e32f9

출처 데이터셋

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08202866B2