Sodium Hydroxide → 4-(N-Boc-N-2-picolylaminomethyl)phenylacetic Acid

HRID 11837Notes

Reaction equation

HRID 11837 reaction equation
[C:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26]C)=[O:25])=[CH:19][CH:18]=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].[OH-].[Na+]>C1COCC1.CO>[C:1]([N:8]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:21][CH:22]=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]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21973576Methyl 4-(N-Boc-N-2-picolylaminomethyl)phenylacetate

Product 1

HCID 219736114-(N-Boc-N-2-picolylaminomethyl)phenylacetic AcidYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 8-3 (83.2 mg) was dissolved in THF (0.8 ml) and methanol (0.8 ml). After the addition of 1 N aqueous solution of sodium hydroxide (0.8 ml), the mixture was stirred for 35 minutes 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, 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 (78.7 mg) as colorless oil.

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. washwashed 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-639408831de942e6a598272ed67cc92c
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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