Water → tert-butyl 4-((1R)-1-aminopropyl)-2-nitrobenzoate

HRID 554826Notes

Reaction equation

HRID 554826 reaction equation
C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.[NH2:11][C@@H:12]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:17]([N+:28]([O-:30])=[O:29])[CH:16]=1)[CH2:13][CH3:14].O.[OH-].[Na+]>C(OCC)(=O)C>[NH2:11][C@@H:12]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[C:17]([N+:28]([O-:30])=[O:29])[CH:16]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86634888tert-butyl 4-((1R)-1-aminopropyl)-2-nitrobenzoate D-tartarate

Product 1

HCID 66934844tert-butyl 4-((1R)-1-aminopropyl)-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 4-((1R)-1-aminopropyl)-2-nitrobenzoate D-tartarate (15g) was suspended in ethyl acetate (75 ml). Water and a 5N aqueous sodium hydroxide solution were added and the mixture stirred and the layers were separated. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then activated carbon was added to the obtained organic layer and the resultant mixture was stirred for 1 hour. The activated carbon was removed by filtration, and the filtrate was concentrated in vacuo to obtain the title compound (8.9 g) as an oily substance. The 1H-NMR spectral data matched those of Example 322.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted again with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additionThen activated carbon was added to the obtained organic layer
  6. stirringthe resultant mixture was stirred for 1 hour
  7. customThe activated carbon was removed by filtration
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4fdbfab1d0ec4b8794350efcab378723
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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