Ethyl Acetate → 6-{[2-(1,3-dioxolan-2-ylmethyl)-1-oxa-5-azaspiro[2.3]hex-5-yl]carbonyl}-2,3-difluoro-N-(2-fluoro-4-iodophenyl)aniline

HRID 1717623노트

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HRID 1717623 반응식
CC(C1C=C(C(C)C)C=C(C(C)C)C=1S([O:19][CH:20]([C:27]1(O)[CH2:30][N:29]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[C:34]=2[NH:41][C:42]2[CH:47]=[CH:46][C:45]([I:48])=[CH:44][C:43]=2[F:49])=[O:32])[CH2:28]1)[CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1)(=O)=O)C.[H-].[Na+].C(OCC)(=O)C>O1CCCC1>[O:26]1[CH2:25][CH2:24][O:23][CH:22]1[CH2:21][CH:20]1[C:27]2([CH2:30][N:29]([C:31]([C:33]3[C:34]([NH:41][C:42]4[CH:47]=[CH:46][C:45]([I:48])=[CH:44][C:43]=4[F:49])=[C:35]([F:40])[C:36]([F:39])=[CH:37][CH:38]=3)=[O:32])[CH2:28]2)[O:19]1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 866212721-[1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]-2-(1,3-dioxolan-2-yl)ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate

생성물 1

HCID 866212736-{[2-(1,3-dioxolan-2-ylmethyl)-1-oxa-5-azaspiro[2.3]hex-5-yl]carbonyl}-2,3-difluoro-N-(2-fluoro-4-iodophenyl)aniline수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

1-[1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]-2-(1,3-dioxolan-2-yl)ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate (50 mg, 0.060 mmol) was dissolved in tetrahydrofuran (1 mL) and was cooled to 0° C. Sodium hydride (60 wt % dispersion in oil; 7 mg, 0.18 mmol) was added and the mixture was stirred at 0° C. for 45 minutes. The mixture was quenched with saturated sodium bicarbonate solution and partitioned with ethyl acetate. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 50% ethyl acetate in hexanes) gave 6-{[2-(1,3-dioxolan-2-ylmethyl)-1-oxa-5-azaspiro[2.3]hex-5-yl]carbonyl}-2,3-difluoro-N-(2-fluoro-4-iodophenyl)aniline (31 mg, 0.057 mmol, 94% yield): MS (EI) for C21H18F3IN2O4: 547 (MH+).

후처리

  1. customThe mixture was quenched with saturated sodium bicarbonate solution
  2. custompartitioned with ethyl acetate
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. washThe combined organic portion was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-873feddafb544fe6b9e3b815ce5f3763
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803839B2

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