Sodium Hydroxide → HCID 67118993, compound

HRID 1189003Notes

Reaction equation

HRID 1189003 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][N:16]=1)=[CH:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66898360HCID 66898360, compound

Product 1

HCID 67118993HCID 67118993, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [2-(7-methoxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (500 mg) was dissolved in a mixture of tetrahydrofuran (5 mL) and ethanol (5 mL). To the mixture was added 1M aqueous sodium hydroxide solution (3 mL) and the mixture was stirred at room temperature for 50 min. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in water and the mixture was washed with diethyl ether. The aqueous layer was acidified with 1M hydrochloric acid (3 mL). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (450 mg, 96%) as a pale yellow solid. MS 462 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washthe mixture was washed with diethyl ether
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-20088ee29efc402084f3eecef45ae66f
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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