Citric Acid → HCID 54268940, Verbindung

HRID 1683051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683051
[CH2:1]([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14](=[O:23])[NH:13][C:12]2=[O:24])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:29]([N:13]1[C:12](=[O:24])[C:11]2([CH2:25][CH2:26][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[N:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:14]1=[O:23])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 311Citric Acid2×HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 53759290HCID 53759290, Verbindung

Produkt 1

HCID 54268940HCID 54268940, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione (12 mmol) and DMF (20 mL). Cool in an ice bath. Add NaH (18 mmol) in several portions. After the addition is complete, add benzyl bromide (18 mmol). Allow the reaction mixture to warm to ambient temperature. After 3 h, cool the reaction vessel using an ice bath and cautiously add 10% aqueous citric acid (20 mL). When gas evolution has ceased, pour into an additional 20 mL of 10% aqueous citric acid and extract using ethyl acetate (3×60 mL). Extract the combined organics with saturated aqueous NaCl, dry over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Purify to obtain the title compound.

Aufarbeitung

  1. temperatureCool in an ice bath
  2. additionAfter the addition
  3. temperaturecool the reaction vessel
  4. extractionextract
  5. extractionExtract the combined organics with saturated aqueous NaCl
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue
  10. customPurify

Quellen und Nachweise

ORD-Eintrag
ord-f78632f6abac4b7fa737f8f91fcdb495
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05635510

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