Butanal → (5-tert-Butoxycarbonylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

HRID 15576Notes

Reaction equation

HRID 15576 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[C:6]([O:10][C:11](=[O:29])[CH2:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][C:15]=1[NH2:28])([CH3:9])([CH3:8])[CH3:7]>C(O)(=O)C.CCO>[C:6]([O:10][C:11](=[O:29])[CH2:12][N:13]1[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][C:15]=2[N:28]=[C:1]1[CH2:2][CH2:3][CH3:4])([CH3:8])([CH3:7])[CH3:9]

Participants

5

Reactant 2

HCID 261ButanalHCID 67199974Glycine,n-[2-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-,1,1-dimethylethyl ester

Product 1

HCID 67199280(5-tert-Butoxycarbonylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Butyraldehyde (0.65 mL, 9.0 mmol) and acetic acid (7 drops) were added to a solution of (2-amino-4-tert-butoxycarbonylamino-phenylamino)-acetic acid tert-butyl ester (2.2 g, 6.5 mmol) in EtOH (100 mL), and stirred overnight at 70° C. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to give the crude sub-title compound that was used without further purification. MS calculated for C21H31N3O4+H: 390, observed: 390.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc04f7d1b41c416f8af2a5442656c18d
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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