Hydrochloric Acid → HCID 23003453, compound

HRID 396549Notes

Reaction equation

HRID 396549 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[N:18](COCC[Si](C)(C)C)[CH:19]=[CH:20][N:21]=1)=[O:16].Cl>CO>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[NH:21][CH:20]=[CH:19][N:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23003287HCID 23003287, compound

Product 1

HCID 23003453HCID 23003453, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl[5-chloro-2-[1-[2-(trimethylsilyl)ethoxymethyl]imidazole-2-carbonyl]-1H-indol-3-yl]acetate (step 1, 300 mg, 0.67 mmol) in methanol (10 ml) was added 2N aqueous HCl (7 ml) and the mixture was refluxed for 1.5 h. After cooling to room temperature, the mixture was concentrated. To the residue was added saturated aqueous sodium bicarbonate (10 ml ) and then the mixture was concentrated. The residual yellow solids were dissolved in THF (100 ml) and dried (MgSO4). Removal of solvent afforded 220 mg (100%) of the title compound as yellow solids.

Workup

  1. temperaturethe mixture was refluxed for 1.5 h
  2. concentrationthe mixture was concentrated
  3. additionTo the residue was added saturated aqueous sodium bicarbonate (10 ml )
  4. concentrationthe mixture was concentrated
  5. dissolutionThe residual yellow solids were dissolved in THF (100 ml)
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-a711d174a05e47b08eb91e177cdd4eba
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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