Sodium Hydroxide → HCID 58975120, compound

HRID 1178920Notes

Reaction equation

HRID 1178920 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-ac2cdf0f133a433cb2b035591485ddc6
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

Loading…