Benzaldehyde → (5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

HRID 15577

Reaktionsgleichung

Reaktionsgleichung von HRID 15577
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23]([O:27][C:28](=[O:43])[CH2:29][N:30]1[C:34]2[CH:35]=[CH:36][C:37]([NH2:39])=[CH:38][C:33]=2[N:32]=[C:31]1[CH2:40][CH2:41][CH3:42])([CH3:26])([CH3:25])[CH3:24]>ClCCCl.O>[C:23]([O:27][C:28](=[O:43])[CH2:29][N:30]1[C:34]2[CH:35]=[CH:36][C:37]([NH:39][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:38][C:33]=2[N:32]=[C:31]1[CH2:40][CH2:41][CH3:42])([CH3:26])([CH3:25])[CH3:24]

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67200153(5-Amino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Produkt 1

HCID 67200053(5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (1.8 g, 8.4 mmol) was added to a solution of benzaldehyde (0.68 mL, 6.5 mmol) and (5-amino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester (1.8 g, 6.5 mmol) in DCE (15 mL), and stirred overnight at room temperature. The reaction solution was diluted with H2O. The organic solution was washed with brine, dried over MgSO4, and concentrated to afford the subtitle compound that was used without further purification. MS calculated for C23H29N3O2+H: 380, observed: 380.

Aufarbeitung

  1. washThe organic solution was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eb1c7c4fd0b249119a8169ad059af745
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732618B2

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