반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.C([Li])CCC.[C:15]([O:19][C:20](=[O:37])[NH:21][CH:22]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[C:23](=[O:28])N(OC)C)([CH3:18])([CH3:17])[CH3:16]>O1CCCC1>[C:15]([O:19][C:20](=[O:37])[NH:21][CH:22]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[C:23]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:9])=[O:28])([CH3:18])([CH3:16])[CH3:17]참가 물질
반응물 3
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- -78 °C
실험 절차
To a stirred solution of 1.75 g (5.78 mmol) 1-bromo-3-fluoro-4-iodo-benzene in 12 ml dry tetrahydrofuran were added at −78° C. 3.61 ml (5.78 mmol) of a 1.6M butyl lithium solution in hexanes. After 1 h 0.600 g (1.65 mmol) rac-[(3,4-dichloro-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester (Intermediate 9) were added and stirred at −78° C. fur further 4 h. Then the reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution, warmed to ambient temperature and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash-chromatography over silica gel with a heptane/AcOEt gradient starting with pure heptane: rac-[2-(4-bromo-2-fluoro-phenyl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester was obtained as a colorless viscous oil: MS (ISP): 476.0 and 477.9 (M+H)+.
후처리
- customThen the reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution
- temperaturewarmed to ambient temperature
- extractionextracted with ethyl acetate
- washThe combined extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
- customThe crude product was purified by flash-chromatography over silica gel with a heptane/AcOEt gradient
출처 및 근거
- ORD 기록
- ord-760c245c50a54948b3aed84b6886ac37
- 출처 데이터셋
- uspto-grants-2013_02
- 특허 번호
- US08367838B2
연결된 노트
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