Diisopropylethylamine → (2-(Pyrid-4-yl)-1h-benzimidazole-4-carbonyl)-(l)-leucine methyl ester

HRID 278031

Reaktionsgleichung

Reaktionsgleichung von HRID 278031
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([OH:18])=O)[C:9]=3[N:8]=2)=[CH:3][CH:2]=1.[B-](F)(F)(F)F.C[CH2:25][O:26][C:27]([C:29]([C:39]#N)=[N:30]OC(N(C)C)=[N+](C)C)=[O:28].[CH:41](N(C(C)C)CC)([CH3:43])[CH3:42]>CN(C=O)C>[CH3:25][O:26][C:27](=[O:28])[C@H:29]([CH2:39][CH:41]([CH3:43])[CH3:42])[NH:30][C:16]([C:15]1[C:9]2[N:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[NH:11][C:10]=2[CH:12]=[CH:13][CH:14]=1)=[O:18]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 112071702-Pyridin-4-yl-3H-benzoimidazole-4-carboxylic acid

Produkt 1

HCID 15480893(2-(Pyrid-4-yl)-1h-benzimidazole-4-carbonyl)-(l)-leucine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

120 mg (0.5 mmol) of 2-(pyrid-4-yl)-1H-benzimidazole-4-carboxylic acid (1d) and 84 mg (0.5 mmol) of H-(L)-leucine methyl ester were dissolved in 5 ml of DMF. 164 mg (0.5 mmol) of TOTU and 0.086 ml of diisopropylethylamine were added and the mixture was stirred at RT for 3 h. The precipitate was filtered off and the filtrate was concentrated. The residue was dissolved in ethyl acetate, the solution was washed with water, and the organic phase was dried using anhydrous sodium sulfate and concentrated. Yield: 180 mg (98%).

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with water
  5. customthe organic phase was dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-184fe2b0b5f24a8d8c53a2db5518b886
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358978B1

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