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

HRID 1398737Notes

Reaction equation

HRID 1398737 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+]>[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])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

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 77%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent3×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 (obtained above) in ethyl acetate (20 mL) was added a 4N solution of hydrogen chloride in ethyl acetate (40 mL) at 0° C., and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate (100 ml) and ethyl acetate (40 mL). The organic layer was separated, washed with water (70 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residual solid was suspended in n-hexane (40 mL), and the suspension was stirred at 60° C. for 30 min and then at room temperature for 1 hr. The resulting solid was collected by filtration and washed with n-hexane to give the title compound (17.9 g, 58.8 mmol, 77%) as a colorless solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (70 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. stirringthe suspension was stirred at 60° C. for 30 min
  6. waitat room temperature for 1 hr
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-5538f8943ecd47edbda69b54286ae9cc
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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