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Ethyl Acetate → N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide

HRID 240966
ノート
印刷プレビュー

反応式

HRID 240966 の反応式
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[C:16](OC)=[CH:15][C:14]([F:19])=[C:13]([F:20])[C:12]=2[NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=C.C[N+]1([O-])CC[O:34][CH2:33]C1.CC[O:40]C(C)=O>C1COCC1.O.[Os](=O)(=O)(=O)=O>[F:20][C:13]1[C:12]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])=[C:11]([NH:10][S:7]([C:4]2([CH2:1][CH:2]([OH:40])[CH2:33][OH:34])[CH2:5][CH2:6]2)(=[O:8])=[O:9])[CH:16]=[CH:15][C:14]=1[F:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 574300741-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclopropane-1-sulfonamide

生成物 1

HCID 15985329N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide収率 78%

試薬・触媒・溶媒 3

HCID 30318
Osmium Tetroxide
触媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

1-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclopropane-1-sulfonamide (97 mg, 0.18 mmol) and 4-methylmorpholine N-oxide (21 mg, 0.18 mmol) were dissolved in THF (8 mL). Osmium tetroxide was added at room temperature (0.018 mmol, 0.13 mL, 4% in H2O) and the reaction mixture was stirred at room temperature for 16 hours. EtOAc was added, the organic phase was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was purified over silica gel chromatography (eluants: EtOAc/MeOH) to obtain the titled product (0.80 g, 78%). 1H NMR (CDCl3, 300 MHz): δ 7.38 (dd, J=1.7 & 10.3 Hz, 1H), 7.26 (m, 1H), 7.14 (s, 1H), 6.87 (s, 1H), 6.53 (dd, J=6.8 & 11.4 Hz, 1H), 6.43 (m, 1H), 4.06 (m, 1H), 3.89 (s, 3H), 3.63 (dd, J=3.7 & 11.1 Hz, 1H), 3.49 (dd, J=6.4 & 11.1 Hz, 1H), 2.3 (dd, J=9.7 & 16.1 Hz, 1H), 1.77 (dd, J=1.9 & 16.0 Hz, 1H), 1.37 (m, 1H), 1.25 (m, 1H), 1.21 (m, 2H), 0.86 (m, 2H); m/z=571 [M−1]−.

後処理

  1. washthe organic phase was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over silica gel chromatography (eluants: EtOAc/MeOH)

出典と根拠

ORDレコード
ord-41421cf5291945278b5f5fbd7092d5e8
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08648116B2

反応ノート

読み込み中…

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