Sodium Hydroxide → HCID 11697284, compound

HRID 1631460Notes

Reaction equation

HRID 1631460 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:29])[CH:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)(=[O:19])=[O:18])[C:9]=1[CH3:28])[CH3:7]>C1COCC1.CO>[Cl:27][C:22]1[CH:21]=[C:20]([S:17]([N:10]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:16]3[C:8]([CH:6]([CH3:7])[C:5]([OH:29])=[O:4])=[C:9]2[CH3:28])(=[O:18])=[O:19])[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219256HCID 67219256, compound

Product 1

HCID 11697284HCID 11697284, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (0.25 mL) is added to a stirring solution of 2-[1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-propionic acid methyl ester (17 mg, 0.04 mmol) in 1:1 THF/MeOH (1 mL). After 4 hours, the reaction is evaporated and the residue dissolved in water. The aqueous solution is acidified to pH 1, and resulting solid is collected by filtration. The crude product is purified by flash chromatography (10:1 EtOAc/MeOH), followed by trituration with iso-hexane, to afford 2-[1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-propionic acid; MH+=413.

Workup

  1. customthe reaction is evaporated
  2. dissolutionthe residue dissolved in water
  3. customresulting solid
  4. filtrationis collected by filtration
  5. customThe crude product is purified by flash chromatography (10:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-359b615d7ccb4c31949cea60235d29d2
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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