Sodium Hydroxide → [5-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic Acid

HRID 546990Notes

Reaction equation

HRID 546990 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:40])[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:38])[CH:25]=3)([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:39])[CH:12]=1.[Cl-].[NH4+]>CO>[CH3:36][C:33]([CH3:34])([CH3:35])[C:32](=[O:37])[CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([C:11]3[CH:12]=[C:7]([CH2:6][C:5]([OH:40])=[O:4])[CH:8]=[N:9][CH:10]=3)=[C:14]([CH3:39])[CH:15]=2)([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:25][C:26]=1[CH3:38]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709040[5-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

Product 1

HCID 57709125[5-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic AcidYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 N sodium hydroxide aqueous solution (0.3 mL) was added to a solution of [5-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester (Example 105-(1); 52.8 mg, 0.10 mmol) in methanol (1.7 mL), and the mixture was stirred for two hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (10% methanol/dichloromethane) to give the title compound (43.2 mg, 84%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by thin layer silica gel chromatography (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a8ff543a04bc498fa76c7fcd1fcb6d8f
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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