Sodium Hydroxide → [1-(4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1754480Notes

Reaction equation

HRID 1754480 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][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:8]=1[CH3:28]>C1COCC1.CO>[CH2:26]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:29])=[O:4])=[C:8]2[CH3:28])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219077[1-(4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Product 1

HCID 11603173[1-(4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (1 ml) is added to a stirring solution of [1-(4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (89 mg, 0.23 mmol) in 1:1 THF/MeOH (4 ml). After 1 hour the reaction is evaporated and the resulting oil is dissolved in water (8 ml) and acidified to pH 3. The resulting precipitate is collected by filtration and dried in vacuo to afford [1-(4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid (MH+373).

Workup

  1. customAfter 1 hour the reaction is evaporated
  2. dissolutionthe resulting oil is dissolved in water (8 ml)
  3. filtrationThe resulting precipitate is collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-95ef516cd9fc4eb7857bb9e8f20b4a16
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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