Sodium Hydroxide → HCID 67706745, compound

HRID 266311Notes

Reaction equation

HRID 266311 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C@@H:14]([CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]CC)=[O:25])=[CH:20][CH:19]=2)=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1>C(O)C>[ClH:3].[C:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C@@H:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[CH:19][CH:20]=1)([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54015094HCID 54015094, compound

Product 1

HCID 67706745HCID 67706745, compoundYield 137.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2N NaOH (2.6 ml) was added to solution of (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-ethoxycarbonylphenyl)-3-(1H-imidazol-1-yl)propanamide (120 mg) in ethanol (10 ml) and the whole was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. A small amount of water was added to the residue, and the whole was concentrated under reduced pressure. The above procedure was repeated 3 times to remove ethanol. The residue was dissolved in 1N HCl (20 ml), and diluted with water (20 ml). Then, the solution was washed 3 times with ethyl acetate (10 ml). The aqueous layer was concentrated under reduced pressure. A small amount of water was added, and the whole was concentrated under reduced pressure. The concentrating steps were repeated 3 times to evaporate excess HCl. The residue was dried under reduced pressure in a desiccator. After ethanol was added, the insoluble materials were removed by filtration. The combined filtrates were concentrated under reduced pressure and dried to obtain (S)-N-(4-carboxyphenyl)-2-(4-chlorobenzenesulfonylamino)-3-(1H-imidazol-1-yl)propanamide hydrochloride (84 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA small amount of water was added to the residue
  3. concentrationthe whole was concentrated under reduced pressure
  4. customto remove ethanol
  5. dissolutionThe residue was dissolved in 1N HCl (20 ml)
  6. additiondiluted with water (20 ml)
  7. washThen, the solution was washed 3 times with ethyl acetate (10 ml)
  8. concentrationThe aqueous layer was concentrated under reduced pressure
  9. additionA small amount of water was added
  10. concentrationthe whole was concentrated under reduced pressure
  11. customto evaporate excess HCl
  12. customThe residue was dried under reduced pressure in a desiccator
  13. additionAfter ethanol was added
  14. customthe insoluble materials were removed by filtration
  15. concentrationThe combined filtrates were concentrated under reduced pressure
  16. customdried

Sources & evidence

ORD record
ord-349b9fd2c03a4d7fbb9f425b6d569e7e
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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