Tetrahydrofuran → HCID 66726076, compound

HRID 1042146Notes

Reaction equation

HRID 1042146 reaction equation
C([O:3][C:4](=[O:38])[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:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[CH:15][C:14]=3[O:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:8][CH2:7]1)C.[OH-].[Na+].O1CCCC1>C(O)C>[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:31][CH:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][C:4]([OH:38])=[O:3])[CH2:7][N:8]=2)=[CH:19]3)=[CH:22][CH:23]=1)(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68090840HCID 68090840, compound

Product 1

HCID 66726076HCID 66726076, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl(2-{5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (424 mg), 1M aqueous sodium hydroxide solution (2 mL), tetrahydrofuran (10 mL), and ethanol (10 mL) was stirred at room temperature for 2 hr. The reaction solution was concentrated under reduced pressure, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was neutralized with 1M hydrochloric acid, 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. The residue was solidified with diethyl ether, and the obtained solid was washed with diethyl ether-hexane to give the title compound (270 mg, yield 67%) as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas added
  3. washthe mixture was washed with ethyl acetate
  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
  9. washthe obtained solid was washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-9753b13efa1745ec91c8f3e08f8e9061
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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