Sodium Hydroxide → 2-(4-((5,6-Diphenyl-2-pyrazinyl)(1-methylethyl)amino)butoxy)acetic acid

HRID 1271304Notes

Reaction equation

HRID 1271304 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:17]1[CH:22]=[N:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:18]=1)[CH:14]([CH3:16])[CH3:15])(C)(C)C.[OH-].[Na+]>CO>[C:23]1([C:20]2[N:21]=[CH:22][C:17]([N:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:6]([OH:35])=[O:5])[CH:14]([CH3:16])[CH3:15])=[N:18][C:19]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69357196Tert-butyl 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)acetate

Product 1

HCID 99318912-(4-((5,6-Diphenyl-2-pyrazinyl)(1-methylethyl)amino)butoxy)acetic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21.07 g of 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester was dissolved in 200 ml of methanol and 60 ml of 1N sodium hydroxide solution was added. After the mixture was heated at reflux for 2 hours, the solvent was evaporated under reduced pressure and the residue was dissolved in water. After washing with diethyl ether, the aqueous layer was neutralized with 60 ml of 1N hydrochloric acid and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure, and then the residue was washed with diisopropyl ether to obtain 15.82 g of the desired compound.

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washAfter washing with diethyl ether
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-e44008ed816f47668b3b617b084c24a0
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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