Sodium Hydroxide → HCID 58975120, compound

HRID 736983Notes

Reaction equation

HRID 736983 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]([CH3:26])[CH3:25])=[CH:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1>C1COCC1.C([O-])(O)=O.[Na+]>[CH:24]([C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]([S:12]([C:9]2[CH:8]=[CH:7][C:6]([C:5]([OH:27])=[O:4])=[CH:11][CH:10]=2)(=[O:13])=[O:14])[CH:16]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58975020HCID 58975020, compound

Product 1

HCID 58975120HCID 58975120, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add five molar NaOH (1.5 mL 0.0075 mol) to a stirring solution of 4-(3-isopropyl-indole-1-sulfonyl)-benzoic acid methyl ester (0.230 g, 0.00061 mol) in THF (10.0 mL) at ambient temperature under N2. Stir the resulting mixture overnight Dilute with 5% NaHCO3 (75 mL) and extract with Et2O. Separate the aqueous layer and acidify with 37% HCl. Extract the resulting precipitate into EtOAc, wash with brine, dry (MgSO4), filter and evaporate giving 0.187 g of the title compound as an off white solid: Mass spectrum (m/e) (M−H) 342.0800; Found (M−H) 342.0802.

Workup

  1. extractionextract with Et2O
  2. customSeparate the aqueous layer
  3. extractionExtract the resulting precipitate into EtOAc
  4. washwash with brine
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. customevaporate

Sources & evidence

ORD record
ord-85ac620044244813a8e06a1a4ce7d588
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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