Sodium Hydroxide → HCID 58081071, compound

HRID 1042162Notes

Reaction equation

HRID 1042162 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:25][CH:26]=2)=[CH:15][C:14]=3[O:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[N:8][CH2:7]1)C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:32][O:31][CH2:30][CH2:29][O:28][CH2:27][C:24]1[N:23]=[CH:22][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:33][CH:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][C:4]([OH:40])=[O:3])[CH2:7][N:8]=2)=[CH:19]3)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58081013HCID 58081013, compound

Product 1

HCID 58081071HCID 58081071, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl{2-[5-({6-[(2-methoxyethoxy)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (190 mg) in ethanol (3 mL) and tetrahydrofuran (3 mL) was added 1N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the concentrate was washed with ethyl acetate. To the aqueous layer was added 1N hydrochloric acid (3 mL), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (157 mg, yield 87%) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe concentrate was washed with ethyl acetate
  3. additionTo the aqueous layer was added 1N hydrochloric acid (3 mL)
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d57e7ea34b3a446db16ba972b3cf9acb
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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