Methanol → 4-(2-(N-Boc-2-picolylamino)ethyl)benzoic Acid

HRID 11842Notes

Reaction equation

HRID 11842 reaction equation
[C:1]([N:8]([CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CO.[OH-].[Na+]>C1COCC1>[C:1]([N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21973679Methyl 4-(2-(N-Boc-N-2-picolylamino)ethyl)benzoate

Product 1

HCID 219736824-(2-(N-Boc-2-picolylamino)ethyl)benzoic AcidYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 9-3 (446.1 mg) was dissolved in THF (4.5 ml) and methanol (4.5 ml) After the addition of 1 mol/l aqueous solution of sodium hydroxide (4.5 ml), the mixture was stirred for 5 hours at room temperature. After the reaction, the solvent was removed by distillation and the residue was dissolved in distilled water. Aqueous solution of hydrochloric acid (1 mol/l) was added to the solution to adjust the pH to 3-4. The settled-down oily product was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was dried under vacuum to obtain the title compound (432.2 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionthe residue was dissolved in distilled water
  4. additionAqueous solution of hydrochloric acid (1 mol/l) was added to the solution
  5. extractionThe settled-down oily product was extracted with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation
  9. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-1c9322052b654c65b143e6b66ad1272d
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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