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Ethyl Acetate → 1-(2,3-Dihydroxypropyl)-N-(3,4,6-trifluoro-2-(2-fluoro-4-iodophenylamino)phenyl)cyclopropane-1-sulfonamide

HRID 73426
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HRID 73426 반응식
[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:4]([NH:10][S:11]([C:14]2([CH2:17]C=C)[CH2:16][CH2:15]2)(=[O:13])=[O:12])[C:5]([F:9])=[CH:6][C:7]=1[F:8].C[N+]1([O-])CC[O:33]CC1.CCO[C:40]([CH3:42])=[O:41]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[OH:33][CH:42]([CH2:40][OH:41])[CH2:17][C:14]1([S:11]([NH:10][C:4]2[C:5]([F:9])=[CH:6][C:7]([F:8])=[C:2]([F:1])[C:3]=2[NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])(=[O:13])=[O:12])[CH2:16][CH2:15]1
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참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 576266441-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenylamino)phenyl]-amide

생성물 1

HCID 159853941-(2,3-Dihydroxypropyl)-N-(3,4,6-trifluoro-2-(2-fluoro-4-iodophenylamino)phenyl)cyclopropane-1-sulfonamide수율 75%

시약·촉매·용매 3

HCID 30318
Osmium Tetroxide
촉매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

1-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenyl amino)-phenyl]-amide (110 mg, 0.21 mmol) and 4-methylmorpholine N-oxide (24.6 mg, 0.21 mmol) was dissolved in THF (8 mL). Osmium tetroxide was added at room temperature (0.021 mmol, 0.153 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 (0.89 g, 75%). 1H NMR (CDCl3, 300 MHz): δ 7.39 (dd, J=1.5 & 10.6 Hz, 1H), 7.29 (d, J=8.8 Hz, 1H), 7.28 (s, 1H), 6.97 (s, 1H), 6.76 (m, 1H), 6.49 (m, 1H), 4.13 (m, 1H), 3.66 (dd, J=3.7 & 11.4 Hz, 1H), 3.53 (dd, J=6.7 & 11.2 Hz, 1H), 2.50(dd, J=10.0 & 16.1 Hz, 1H), 1.6 (m, 1H), 1.46 (m, 1H), 1.28 (m, 1H), 1.20 (m, 2H), 0.92 (m, 2H); m/z=559 [M−1]−.

후처리

  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)

출처 및 근거

ORD 기록
ord-ad21af6496994eb8b9df0d184163c99a
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08829052B2

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