Sodium Hydroxide → HCID 11530248, compound

HRID 1631490Notes

Reaction equation

HRID 1631490 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:23])=[O:22])=[CH:17][CH:16]=2)[C:6]=1[CH3:24].[OH-].[Na+]>C1COCC1.CO>[CH3:23][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:7]2[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:13]3[C:5]([CH2:4][C:3]([OH:25])=[O:2])=[C:6]2[CH3:24])=[CH:16][CH:17]=1)=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219831HCID 67219831, compound

Product 1

HCID 11530248HCID 11530248, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of [1-(4-methanesulfinyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.340 g, 0.95 mmol) in THF/MeOH (8 ml of a 1:1 mixture) is added 1M NaOH (2 ml) and the reaction mixture is stirred for 2 hours. The solvent is removed in vacuo and the resulting oil is dissolved in water and acidified to pH2 using concentrated HCl. A precipitate forms which is filtered, washed with water and dried in vacuo to yield the titled product. (MH+ 343)

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resulting oil is dissolved in water
  3. filtrationA precipitate forms which is filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-184b100e29034f0dbcaf96164a5d4776
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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