Diisopropylethylamine → HCID 21904463, Verbindung

HRID 1247782

Reaktionsgleichung

Reaktionsgleichung von HRID 1247782
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]([CH2:13][CH2:14][OH:15])[C:11]=1[NH2:12].C(N(C(C)C)C(C)C)C.[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][C:35](ON1C(=O)CCC1=O)=[O:36])=[O:31])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[NH2:12][C:11]1[N:10]([CH2:13][CH2:14][OH:15])[N:9]=[CH:8][C:7]=1[NH:6][C:35](=[O:36])[CH2:34][CH2:33][NH:32][C:30]([O:29][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:31]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10684599Boc-Beta-Ala-OSuHCID 116731484,5-Diamino-1-(2-hydroxyethyl)pyrazole sulfate

Produkt 1

HCID 21904463HCID 21904463, VerbindungAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a suspension of 4,5-diamino-1-(2-hydroxyethyl)pyrazole sulfuric acid salt (2.4 g) in methylene chloride (40 ml) were added N-ethyldiisopropylamine (2.1ml) and N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (2.3 g) under ice-cooling, and the mixture was stirred at room temperature for 6 hours. To the reaction mixture were added brine (40 ml) and saturated aqueous sodium hydrogen carbonate solution (20 ml), and the mixture was extracted with a mixture of ethyl acetate and 2-propanol, (3:1, 60 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with diethyl ether to give 5-amino-4-[3-(tert-butoxycarbonylamino)propionyl]amino-1-(2-hydroxyethyl)pyrazole (1.65 g) as a solid.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with a mixture of ethyl acetate and 2-propanol, (3:1, 60 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5cc67e9a7c17493e91fff3aad5122c36
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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