Methanol → HCID 58081018, compound

HRID 1042195Notes

Reaction equation

HRID 1042195 reaction equation
C([O:3][C:4](=[O:33])[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]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)=[CH:15][C:14]=3[CH2:31][CH3:32])=[N:8][CH2:7]1)C.CO.[OH-].[K+]>O1CCCC1>[CH2:31]([C:14]1[CH:15]=[C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][CH:26]=2)[CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:9]1[S:10][CH:6]([CH2:5][C:4]([OH:33])=[O:3])[CH2:7][N:8]=1)=[CH:19]2)[CH3:32]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 58081050ethyl[2-(7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate

Product 1

HCID 58081018HCID 58081018, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[2-(7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (3.0 g), methanol (15 mL), and tetrahydrofuran (30 mL) was added an aqueous solution (10 mL) of potassium hydroxide (1.1 g), and the mixture was stirred at room temperature for 15 hr. The reaction solution was concentrated, acidified with aqueous citric acid solution, 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 obtained pale-yellow crystals were washed with ethyl acetate-hexane to give the title compound (2.5 g, yield 88%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe obtained pale-yellow crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-a6d27d63eea8497eab0f022a2b71cff1
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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