Sodium Hydroxide → HCID 11618107, compound

HRID 1254874Notes

Reaction equation

HRID 1254874 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:29])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][C:14]=2[Cl:16])[N:9]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[C:8]=1[CH3:28]>C1COCC1.CO>[Cl:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]2[N:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:8]([CH3:28])=[C:7]([CH2:6][C:5]([OH:29])=[O:4])[C:15]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219495HCID 67219495, compound

Product 1

HCID 11618107HCID 11618107, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (0.5 ml) is added to a stirring solution of [4-chloro-1-(4-methanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (38 mg, 0.093 mmol) in 1:1 THF/MeOH (1 ml). After stirring at room temperature for 4 hours, the reaction mixture is filtered to remove any undissolved material and is evaporated to dryness. The resulting oil is dissolved in water (1 ml) and acidified to pH 2. The resulting precipitate collected by filtration and dried in vacuo to afford [4-chloro-1-(4-methanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid. (MH+ 393)

Workup

  1. filtrationthe reaction mixture is filtered
  2. customto remove any undissolved material
  3. customis evaporated to dryness
  4. dissolutionThe resulting oil is dissolved in water (1 ml)
  5. filtrationThe resulting precipitate collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6d6f31a8b55249baafcd80c42716f337
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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