Sodium Hydroxide → 5-(3,5-Di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylic acid

HRID 1844715Notes

Reaction equation

HRID 1844715 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([C:17]2[N:21]([S:22]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:24])=[O:23])[C:20]([CH3:31])=[C:19]([C:32]([O:34]CC)=[O:33])[CH:18]=2)[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4]>O.CO>[C:13]([C:11]1[CH:10]=[C:9]([C:17]2[N:21]([S:22]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)(=[O:24])=[O:23])[C:20]([CH3:31])=[C:19]([C:32]([OH:34])=[O:33])[CH:18]=2)[CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:12]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86719131Ethyl 5-(3,5-di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 708727905-(3,5-Di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of NaOH (2.72 g, 67.8 mmol) in H2O was added to compound 4c (800 mg, 1.7 mmol) in MeOH (60 mL) and refluxed for 3 h, evaporated, diluted with H2O, acidified with conc. HCl to pH ˜2, extracted with EA (3×30 mL), washed by brine, dried with Na2SO4 and concentrated to get the compound 4d (700 mg, 90%) as a white solid.

Workup

  1. temperaturerefluxed for 3 h
  2. customevaporated
  3. additiondiluted with H2O
  4. extractionextracted with EA (3×30 mL)
  5. washwashed by brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-99a885e08ee2442fb7b329d71839f212
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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