Sodium Chloride → HCID 86593418, Verbindung

HRID 1247846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247846
S(O)(O)(=O)=O.[F:6][CH2:7][CH2:8][N:9]1[C:13]([NH2:14])=[C:12]([NH2:15])[CH:11]=[N:10]1.O=C1CCC(=O)N1[O:23][C:24](=O)[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].C(=O)([O-])O.[Na+].[Cl-].[Na+]>O1CCCC1>[NH2:14][C:13]1[N:9]([CH2:8][CH2:7][F:6])[N:10]=[CH:11][C:12]=1[NH:15][C:24](=[O:23])[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 10684599Boc-Beta-Ala-OSuHCID 69462687HCID 69462687, Verbindung

Produkt 1

HCID 86593418HCID 86593418, VerbindungAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 1-(2-fluoroethyl)-1H-pyrazole-4,5-diamine sulfate (3 g) in tetrahydrofuran (30 ml) were added tert-butyl {3-[(2,5-dioxo-1-pyrrolidinyl)oxy]-3-oxopropyl}carbamate (3.9 g) and N,N-diisoporpylethylamine (3.5 g) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours. An aqueous sodium hydrogen carbonate solution and sodium chloride were added, and the mixture was extracted with ethyl acetate-tetrahydrofuran (three times). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=8:1) to give tert-butyl (3-{[5-amino-1-(2-fluoroethyl)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (2.3 g).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran (three times)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-096a1cd3f0504a95be7ba41c1050b414
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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