Hydrochloric Acid → Isopropyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

HRID 1698571Notes

Reaction equation

HRID 1698571 reaction equation
[CH2:1]([CH:3]([C:6]1[C:14]2[N:13]([CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[C:12](=[O:22])[N:11](C(OC(C)(C)C)=O)[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH:19]([O:18][C:16](=[O:17])[CH2:15][N:13]1[C:14]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[CH:9][C:10]=2[NH:11][C:12]1=[O:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67273576tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

Product 1

HCID 86632855Isopropyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetateYield 85.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (8.95 g, 22.1 mmol) in ethyl acetate (10 ml) was added a 4N solution of hydrogen chloride in ethyl acetate (20 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 5-20% ethyl acetate/hexane gradient mixture. The residual solid was washed with hexane to give 5.76 g (18.9 mmol, 85.6%) of the title compound as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate (X2)
  2. washThe combined organic layer was washed with brine (X1)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 5-20% ethyl acetate/hexane gradient mixture
  7. washThe residual solid was washed with hexane

Sources & evidence

ORD record
ord-a7aff7ea13304572a19bddd64bb6eab7
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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