Dimethylformamide → 1-formyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N,N-diisopropyl-2-naphthamide

HRID 1061881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061881
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]([N:42]([CH:46]([CH3:48])[CH3:47])[CH:43]([CH3:45])[CH3:44])=[O:41])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].CN(C)CCN(C)C.CCCCCC.C([Li])CCC.CN([CH:71]=[O:72])C>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH:71]([C:36]1[C:37]2[C:32](=[CH:31][C:30]([C:2]([OH:1])([C:6]3[N:7]=[CH:8][N:9]([C:11]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:10]=3)[CH:3]([CH3:5])[CH3:4])=[CH:39][CH:38]=2)[CH:33]=[CH:34][C:35]=1[C:40]([N:42]([CH:43]([CH3:45])[CH3:44])[CH:46]([CH3:48])[CH3:47])=[O:41])=[O:72]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 222850636-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N,N-diisopropyl-2-naphthamideHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 222850501-formyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N,N-diisopropyl-2-naphthamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution (1000 mL) of 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N,N-diisopropyl-2-naphthamide (50.0 g) and N,N,N′,N′-tetramethylethylenediamine (94.9 mL) in toluene was added dropwise a butyllithium hexane solution (1.6 M: 196 mL) at −70° C. After stirring at the same temperature for 2 hrs., DMF (60.9 mL) was added dropwise and mixture was stirred for 20 min. Water was added to the reaction solution and the mixture was diluted with ethyl acetate. The organic layer was washed successively with water, 10% aqueous citric acid solution, water and saturated aqueous sodium hydrogen carbonate, and dried over magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from hexane-ethyl acetate (3:1) to give the title compound (36.0 g) as a colorless powder.

Aufarbeitung

  1. stirringmixture was stirred for 20 min
  2. washThe organic layer was washed successively with water, 10% aqueous citric acid solution, water and saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was recrystallized from hexane-ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-a0e6a6877af14d4997691fb866059a10
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960586B2

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