Hydrogen Peroxide → Oxo-enzalutamide

HRID 38758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38758
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[N:11]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([NH:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=3)[C:10]2=S)=[CH:5][C:4]=1[C:29]([F:32])([F:31])[F:30])#[N:2].[OH:33]O>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[N:11]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([NH:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=3)[C:10]2=[O:33])=[CH:5][C:4]=1[C:29]([F:32])([F:31])[F:30])#[N:2]

Komponenten

4

Edukt 2

HCID 784Hydrogen PeroxideHCID 15951529Enzalutamide

Produkt 1

HCID 46898524Oxo-enzalutamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide (1.52 g, 3.4 mmol) in ethanol (60 mL) was added 30% aqueous H2O2 (30 mL) at room temperature. The solution was heated to reflux for 1 h. After removal of ethanol, brine (100 mL) was added and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product that was purified by silica gel chromatography. MS (m/z), 449 (M+1). HPLC: Column, YMC ODS A, 4.6×150 mm, 5 μm, Mobile Phase A:10 mM Ammonium acetate, Mobile Phase B: Acetonitrile, Gradient, 10% B up to 2 min, 10% to 90% B in 3 min, hold for 3 min, 90% to 10% B in 5 min, Retention time, 8.976 min, HPLC Purity, 98.46%, Flow Rate, 1 mL/min. 1H NMR (CDCl3, Freebase): δ (ppm) 8.22 (t, 1H), 8.18 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.28 (d, 1H), 7.22 (d, 1H), 6.70 (m, 1H), 3.05 (d, 3H), 1.65 (s, 6H).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. customAfter removal of ethanol, brine (100 mL)
  4. additionwas added
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9e3a5d226e54429e9a5a279e1a52ee55
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524755B2

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