Sodium Hydroxide → [4-({Butyl[6-(4-methylphenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetic acid

HRID 1269689Notes

Reaction equation

HRID 1269689 reaction equation
[CH2:1]([N:5]([CH2:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:22]([CH3:33])[CH:21]=1)[C:6]1[CH:11]=[N:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([N:5]([CH2:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:22]([CH3:33])[CH:21]=1)[C:6]1[CH:11]=[N:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622854Ethyl [4-({butyl[6-(4-methylphenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448316[4-({Butyl[6-(4-methylphenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetic acidYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({butyl[6-(4-methylphenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetate (39 mg, 0.087 mmol) in methanol (1 mL) and tetrahydrofuran (1 mL), was added 2M sodium hydroxide (1 mL). After shaking for 1 h at room temperature the solvent was evaporated and the residue was then acidified with 2M HCl and extracted CH2Cl2 (2×10 mL). The organic solution separated by hydrophobic frit and the solvents removed in vacuo to afford the title compound as a bright yellow solid (34 mg).

Workup

  1. customwas evaporated
  2. extractionextracted CH2Cl2 (2×10 mL)
  3. customThe organic solution separated by hydrophobic frit
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-fe984526eb9e4cc7b978b7e0e53100b7
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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