Sodium Hydroxide → HCID 11697284, compound

HRID 1754462Notes

Reaction equation

HRID 1754462 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-d498d1853c3f47b3a3a696a5eb1f119e
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

Loading…