Ethyl Acetate → HCID 86621265、化合物

HRID 1808989ノート

反応式

HRID 1808989 の反応式
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]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86621264HCID 86621264、化合物

生成物 1

HCID 86621265HCID 86621265、化合物収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-2c5adc583da14a18ba054ed6d8b7bf82
出典データセット
uspto-grants-2013_01
特許番号
US08362002B2

反応ノート

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