Sodium Hydroxide → HCID 67118679, compound

HRID 1189008Notes

Reaction equation

HRID 1189008 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:25]=[N:26][C:27]([CH2:30][O:31][CH3:32])=[CH:28][CH:29]=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:25]=[N:26][C:27]([CH2:30][O:31][CH3:32])=[CH:28][CH:29]=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 70963859HCID 70963859, compound

Product 1

HCID 67118679HCID 67118679, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [2-(7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (1.36 g) was dissolved in a mixture of tetrahydrofuran (15 mL) and ethanol (15 mL). To the mixture was added 1M aqueous sodium hydroxide solution (5 mL) and the mixture was stirred at room temperature for 30 min. The mixture was concentrated under reduced pressure. The residue was dissolved in water and the mixture was neutralized with 1M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (1.30 g, 100%) as a yellow amorphous solid. MS 428 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-701458dfd3a1435e9db0fc4f40a67f8d
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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