Sodium Hydroxide → HCID 11697284, compound

HRID 1445572Notes

Reaction equation

HRID 1445572 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-814044e93d69445db95ddb8ae2ade0d7
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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