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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 508144
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 508144
[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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Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318
Osmium Tetroxide
Katalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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]−.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-aec86c9b08b744ed8e568b3943152431
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09095581B2

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