1,2-Dichloroethane → N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(2,2-dimethylpropyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244964

Reaktionsgleichung

Reaktionsgleichung von HRID 2244964
[CH3:1][C:2]([CH3:10])([CH3:9])[CH2:3][C@@H:4]([C:6]([OH:8])=O)[NH2:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1.[CH3:21][N:22]1[CH2:26][CH2:25][N:24]=[C:23]1[C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.C(Cl)CCl>CN(C=O)C.O>[CH3:21][N:22]1[CH2:26][CH2:25][N:24]=[C:23]1[C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:6](=[O:8])[CH:4]([CH2:3][C:2]([CH3:1])([CH3:10])[CH3:9])[NH:5][C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)=[O:20])=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 76934-Chlorophenyl IsocyanateHCID 194032(2S)-2-Amino-4,4-dimethylpentanoic acidHCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

Produkt 1

HCID 11619441N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(2,2-dimethylpropyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of DL-γ-methylleucine (48 mg, 0.33 mmol) in DMF (2 mL), 4-chlorophenyl isocyanate (50 mg, 0.33 mmol) was added. The mixture was then stirred at room temperature overnight. To the reaction mixture, 4-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine (150 mg, 0.86 mmol) and H2O (0.5 mL, to solubilize the amine) were added. To the solution, EDC (127 mg, 0.66 mmol) was added. After being stirred at room temperature overnight, the solution was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (77 mg). MS 456.2 and 458.2 (M+H, Cl pattern).

Aufarbeitung

  1. additionwere added
  2. stirringAfter being stirred at room temperature overnight
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a345ab8f0ba0495198f2a0545a6e7e11
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678913B2

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