Hydrochloric Acid → 2-Methyl-2-({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}oxy)propanoic acid

HRID 1391807Notes

Reaction equation

HRID 1391807 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[N:23]=2)[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=1[CH3:38])([CH3:8])[C:3]([O:5]CC)=[O:4].O.[OH-].[Na+].Cl>C1COCC1>[NH3:23].[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=3)[N:23]=2)[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=1[CH3:38])([CH3:8])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69207846HCID 69207846, compound

Product 2

HCID 222AmmoniaYield 10%HCID 100062142-Methyl-2-({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}oxy)propanoic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-methyl-2-({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}oxy)propanoate (9 mg, 0.02 mmol) was dissolved in THF (0.75 mL), water (0.25 mL) and aqueous NaOH (2M, 35 μl, 0.07 mmol) and the mixture heated at 80° C. for 16 hours. More aqueous NaOH (2M, 420 μl, 0.84 mmol) was then added and heating continued for an additional 24 hours. The mixture was then cooled, neutralised with aqueous HCl (2M), partitioned between EtOAc and water and the layers separated. The organic layer was then washed with brine, dried (Na2SO4) and reduced to give a pale yellow oil. Purification by SPE (aminopropyl, 1 g cartridge) loading in CHCl3 and eluting with dioxane and then 10% aqueous ammonia in dioxane afforded the title compound as a colourless gum (4.5 mg).

Workup

  1. temperatureheating
  2. temperatureThe mixture was then cooled
  3. custompartitioned between EtOAc and water
  4. customthe layers separated
  5. washThe organic layer was then washed with brine
  6. dry with materialdried (Na2SO4)
  7. customto give a pale yellow oil
  8. customPurification by SPE (aminopropyl, 1 g cartridge) loading in CHCl3
  9. washeluting with dioxane

Sources & evidence

ORD record
ord-b383acf8f9d6468aafe5024b6294ef8b
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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