Methanol → 4-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoic acid

HRID 11836Notes

Reaction equation

HRID 11836 reaction equation
[C:1]([N:8]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[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].CO.[OH-].[Na+]>C1COCC1>[C:1]([N:8]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=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 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21973580methyl 4-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoate

Product 1

HCID 219736504-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoic acidYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 1-1 (200.6 mg) was added with methanol (2 ml), THF (2 ml), and 1 mol/l aqueous solution of sodium hydroxide (2 ml), and the mixture was stirred for one day at room temperature. After the completion of the reaction, the solvent was removed by distillation and water (5 ml) was added. Aqueous solution of hydrochloric acid (1 mol/l) was added dropwise to the resulting solution to adjust the pH to 3. The deposited crystals were collected by filtration and dried to obtain the title compound (123.2 mg) as colorless crystals.

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was removed by distillation and water (5 ml)
  3. additionwas added
  4. additionAqueous solution of hydrochloric acid (1 mol/l) was added dropwise to the resulting solution
  5. filtrationThe deposited crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-d2bf217eddca4257ae51da4d5cb2c928
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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