Sodium Hydroxide → HCID 19032858, compound

HRID 266331Notes

Reaction equation

HRID 266331 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH:14]([CH2:29][O:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=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])[CH: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][O:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:19][CH:20]=1)([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19032723HCID 19032723, compound

Product 1

HCID 19032858HCID 19032858, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2N NaOH (143 μl) was added to a solution of (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-ethoxycarbonylphenyl)-3-(pyridin-3-yloxy)propanamide (48.1 mg) in ethanol (5 ml), and the whole was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. A small amount of purified water was added to the residue, and the mixture was concentrated under reduced pressured. The concentration step was repeated 3 times to remove ethanol. The residue was dissolved in 1N HCl (20 ml), diluted with water (20 ml), and then washed 3 times with ethyl acetate (10 ml). The aqueous layer was concentrated under reduced pressure. A small amount of purified water was added, and the mixture was concentrated under reduced pressure. The concentrating step was repeated 3 times to evaporate excess HCl. The residue was dried under reduced pressure in a desiccator, and ethanol was added. The insoluble materials were removed by filtration. The combined filtrates were concentrated and dried under reduced pressure to obtain (RS)-N-(4-carboxyphenyl)-2-(4-chlorobenzenesulfonylamino)-3-(pyridin-3-yloxy)propanamide hydrochloride (21.8 mg).

Workup

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

Sources & evidence

ORD record
ord-3dc536f413a54ae196838692ee4dd709
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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