Water → (2R,5S,Z)-3-(2-{4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(prop-1-en-1-yl)phenyl]-2,5-dimethylpiperazin-1-yl}-2-oxoethyl)-5-(4-isopropoxyphenyl)-5-methylimidazolidine-2,4-dione

HRID 1038561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038561
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:18])[NH:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:7][CH:6]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([N:29]1[CH2:34][C@H:33]([CH3:35])[N:32]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([O:51]COC)([C:47]([F:50])([F:49])[F:48])[C:43]([F:46])([F:45])[F:44])=[CH:38][C:37]=2/[CH:55]=[CH:56]\[CH3:57])[CH2:31][C@H:30]1[CH3:58])=[O:28].O>CN(C)C=O>[F:45][C:43]([F:44])([F:46])[C:42]([C:39]1[CH:40]=[CH:41][C:36]([N:32]2[CH:33]([CH3:35])[CH2:34][N:29]([C:27](=[O:28])[CH2:26][N:13]3[C:12](=[O:17])[C@@:11]([C:8]4[CH:7]=[CH:6][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[CH:10][CH:9]=4)([CH3:18])[NH:15][C:14]3=[O:16])[C@H:30]([CH3:58])[CH2:31]2)=[C:37](/[CH:55]=[CH:56]\[CH3:57])[CH:38]=1)([OH:51])[C:47]([F:50])([F:49])[F:48]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30521535-methyl-5-[4-(propan-2-yloxy)phenyl]imidazolidine-2,4-dioneHCID 86647204(2R,5S,Z)-2-bromo-1-(4-{4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-(prop-1-en-1-yl)phenyl}-2,5-dimethylpiperazin-1-yl)ethanone

Produkt 1

HCID 86647203(2R,5S,Z)-3-(2-{4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(prop-1-en-1-yl)phenyl]-2,5-dimethylpiperazin-1-yl}-2-oxoethyl)-5-(4-isopropoxyphenyl)-5-methylimidazolidine-2,4-dioneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-[4-(1-Methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione (7.7 mg, 0.0311 mmol) was dissolved in N,N-dimethylformamide (500 μL), added potassium carbonate (8.6 mg, 0.0622 mmol) under ice-cold conditions, and the mixture was stirred at room temperature for 5 minutes. Then, under ice-cold conditions, (2R,5S,Z)-2-bromo-1-(4-{4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-(prop-1-en-1-yl)phenyl}-2,5-dimethylpiperazin-1-yl)ethanone (17 mg, 0.0311 mmol) was added and stirred at room temperature for 18 hours. Under ice-cold conditions, the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was dissolved in ethyl acetate (1.0 mL), added a solution of 4N-hydrochloric acid-ethyl acetate (1.0 mg), and the mixture was stirred at room temperature for 1 hour. Under ice-cold conditions, the reaction solution was added water and a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (17.4 mg (yield 83%)) was obtained as a yellow oil.

Aufarbeitung

  1. stirringstirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe obtained residue was dissolved in ethyl acetate (1.0 mL)
  7. additionadded a solution of 4N-hydrochloric acid-ethyl acetate (1.0 mg)
  8. stirringthe mixture was stirred at room temperature for 1 hour
  9. additionUnder ice-cold conditions, the reaction solution was added water
  10. extractiona saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c4014e49cfc94f2b8d6ce58110303ff4
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551985B2

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