Ethyl Acetate → HCID 86621265, 화합물

HRID 1808989노트

반응식

HRID 1808989 반응식
CC(C1C=C(C(C)C)C=C(C(C)C)C=1S(O[CH:20]([C:22]1([OH:45])[CH2:25][N:24]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[C:29]=2[NH:36][C:37]2[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:38]=2[F:44])=[O:27])[CH2:23]1)[CH3:21])(=O)=O)C.[H-].[Na+].C(OCC)(=O)C>O1CCCC1>[F:35][C:30]1[C:31]([F:34])=[CH:32][CH:33]=[C:28]([C:26]([N:24]2[CH2:25][C:22]3([O:45][CH:20]3[CH3:21])[CH2:23]2)=[O:27])[C:29]=1[NH:36][C:37]1[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:38]=1[F:44]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86621264HCID 86621264, 화합물

생성물 1

HCID 86621265HCID 86621265, 화합물수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

1-[1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate (194 mg, 0.256 mmol) was dissolved in tetrahydrofuran (2 mL) and was cooled to 0° C. Sodium hydride (60 wt % dispersion in oil; 31 mg, 0.775 mmol) was added and the mixture was stirred at 0° C. for 15 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 2,3-difluoro-N-(2-fluoro-4-iodophenyl)-6-[(2-methyl-1-oxa-5-azaspiro[2.3]hex-5-yl)carbonyl]aniline (120 mg, 0.253 mmol, 99% yield): MS (EI) for C18H14F3IN2O2: 475 (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-2c5adc583da14a18ba054ed6d8b7bf82
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362002B2

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