Sodium Hydroxide → 2-(5-hexyloxy-1H-indol-2-yl)thio-2-phenylpropionic acid

HRID 846672Notes

Reaction equation

HRID 846672 reaction equation
[CH2:1]([O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[C:17](=[O:27])[C:18]([CH3:26])([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[S:19][C:12]3=[CH:11][C:10]=2[CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-:28].[Na+]>>[CH2:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([S:19][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:26])[C:17]([OH:28])=[O:27])=[CH:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 157249707-hexyloxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one

Product 1

HCID 157249712-(5-hexyloxy-1H-indol-2-yl)thio-2-phenylpropionic acidYield 93%

Procedure

To 7-hexyloxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one (3.92 g), 2N sodium hydroxide (70 ml) was added, and the mixture was heated and refluxed for 1.5 hours. The reaction mixture was allowed to cool, and the deposited crystalline matter was collected by filtration. The crystalline matter was dissolved in methanol. The solution was made acidic by adding concentrated hydrochloric acid under ice cooling, and the solvent was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, to give 3.81 g (yield: 93 %) of the desired compound as a colorless powder. The melting point was 100°-102° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 1.5 hours
  3. temperatureto cool
  4. filtrationthe deposited crystalline matter was collected by filtration
  5. dissolutionThe crystalline matter was dissolved in methanol
  6. additionby adding concentrated hydrochloric acid under ice cooling
  7. customthe solvent was evaporated under reduced pressure
  8. additionWater was added to the residue
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e46542b6018a4025aa8d29ad08c6eb0c
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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