1,1'-Carbonyldiimidazole → HCID 67502797, Verbindung

HRID 1887198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887198
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[C:24]([O:28][C:29](=[O:34])[C@@H:30]([NH2:33])[CH2:31][CH3:32])([CH3:27])([CH3:26])[CH3:25]>N1C=CC=CC=1.O>[C:24]([O:28][C:29](=[O:34])[C@@H:30]([NH:33][C:8]([C:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH2:31][CH3:32])([CH3:26])([CH3:25])[CH3:27]

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 738363-Aminopicolinic acidHCID 53628861tert-Butyl (2S)-2-aminobutanoate--hydrogen chloride (1/1)

Produkt 1

HCID 67502797HCID 67502797, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 276 mg of 3-aminopyridine-2-carboxylic acid in pyridine (3.0 mL) is added 324 mg of 1,1′-carbonyldiimidazole. The mixture is stirred at room temperature for 2 h. Then 391 mg of (S)-2-amino-butyric acid tert-butyl ester hydrochloride is added and the mixture is stirred for 16 h at room temperature. Then the reaction mixture is diluted with water (1 mL) and concentrated. The residue is diluted with additional 5 mL water and the product is extracted with ethyl acetate (3×5 mL). The combined organic layers are washed with brine, dried (sodium sulfate) and concentrated. The residue is purified by flash chromatography on silica gel to give 218 mg (39%) of (S)-2-[(3-amino-pyridine-2-carbonyl)-amino]-butyric acid tert-butyl ester.

Aufarbeitung

  1. stirringthe mixture is stirred for 16 h at room temperature
  2. concentrationconcentrated
  3. additionThe residue is diluted with additional 5 mL water
  4. extractionthe product is extracted with ethyl acetate (3×5 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-071887fec533412581cffc80d03b50ea
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501749B2

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