Water → (1-[4-(3-Chloro-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

To a stirred solution of {1-[4-(6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (5 mg, 0.01 mmol) in EtOH (1 mL), was added sodium hypochlorite (10% aqueous solution, 0.4 mL) at RT. After 2 h, EtOAc and water were added. The resulting biphasic mixture was separated. The aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The reaction was repeated with {1-[4-(6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (20 mg, 0.039 mmol) and aqueous sodium hypochlorite (2 mL) in EtOH (3 mL) with initial cooling in a cold water bath. After workup, the resultant residues were combined and subjected to flash chromatography (SiO2, gradient 20 to 40% EtOAc in cyclohexane) to afford the title compound (16 mg, 60%) as a white solid. LCMS (Method H): RT=4.39 min, [M+H]+=542/544.

1. customThe resulting biphasic mixture was separated
2. extractionThe aqueous phase was extracted with EtOAc
3. washThe combined organic extracts were washed with water and brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. temperaturewith initial cooling in a cold water bath

ORD 기록

ord-0f0335fc80f141cf946c92c801d2468e

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08546376B2