Sodium Hydroxide → HCID 66897332, compound

HRID 1188928Notes

Reaction equation

HRID 1188928 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH2:30][O:31][CH3:32])[O:5][C:6]1[CH:7]=[C:8]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11]2.[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:1][O:2][CH2:3][CH:4]([CH2:30][O:31][CH3:32])[O:5][C:6]1[CH:7]=[C:8]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66897808HCID 66897808, compound

Product 1

HCID 66897332HCID 66897332, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (3.42 g) in a mixture of tetrahydrofuran (20 mL) and ethanol (15 mL) was added 1M aqueous sodium hydroxide solution (18 mL), and the mixture was stirred at 50° C. for 50 min. The mixture was concentrated under reduced pressure and the residue was dissolved in water. The mixture was washed with diethyl ether. To the aqueous layer was added 1M hydrochloric acid (18.5 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual amorphous solid was solidified with diethyl ether to give the title compound (1.66 g) as a pale yellow solid. MS 553 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washThe mixture was washed with diethyl ether
  4. additionTo the aqueous layer was added 1M hydrochloric acid (18.5 mL)
  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

Sources & evidence

ORD record
ord-1c01bc76d7f54ec4868130782f106174
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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