Water → Bicalutamide

HRID 1269473

Reaktionsgleichung

Reaktionsgleichung von HRID 1269473
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].[OH2:28].[OH:29]OS([O-])=O.[K+]>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:29])=[O:28])=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 9800987Bicalutamide sulfideHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 2375Bicalutamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 40 g (0.1 mol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 600 ml of methanol and 400 ml of water 100 g (0.16 mol) of Oxone® oxidizing agent [2KHSO5KHSO4K2SO4 salt] was added. The reaction mixture was stirred at 25° C. for 6 h, then the methanol was distilled off under diminished pressure and the residue was extracted twice with 500 ml of dichloromethane. The organic layer was washed twice with 400 ml of 10% aqueous sodium thiosulfate solution, then with brine, dried over sodium sulfate and concentrated under diminished pressure. The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C.

Aufarbeitung

  1. additionwas added
  2. distillationthe methanol was distilled off under diminished pressure
  3. extractionthe residue was extracted twice with 500 ml of dichloromethane
  4. washThe organic layer was washed twice with 400 ml of 10% aqueous sodium thiosulfate solution
  5. dry with materialwith brine, dried over sodium sulfate
  6. concentrationconcentrated under diminished pressure
  7. customThe residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which

Quellen und Nachweise

ORD-Eintrag
ord-fb8594b35111463695d5b9ec3615ff96
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199257B1

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