Hydrochloric Acid → (4-{4-[(4-[({4-[(E)-2-(1-ethyl-1H-imidazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetic acid

HRID 2222010Notes

Reaction equation

HRID 2222010 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([O:21][CH2:22][C:23]3[CH:48]=[CH:47][C:26]([O:27][CH2:28][C:29]4[N:30]=[C:31]([C:35]5[CH:40]=[CH:39][C:38]([CH2:41][C:42]([O:44]CC)=[O:43])=[CH:37][CH:36]=5)[O:32][C:33]=4[CH3:34])=[C:25]([O:49][CH3:50])[CH:24]=3)=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[N:5]=[CH:4]1)[CH3:2].[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:1]([N:3]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([O:21][CH2:22][C:23]3[CH:48]=[CH:47][C:26]([O:27][CH2:28][C:29]4[N:30]=[C:31]([C:35]5[CH:40]=[CH:39][C:38]([CH2:41][C:42]([OH:44])=[O:43])=[CH:37][CH:36]=5)[O:32][C:33]=4[CH3:34])=[C:25]([O:49][CH3:50])[CH:24]=3)=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[N:5]=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86605922HCID 86605922, compound

Product 1

HCID 69214960(4-{4-[(4-[({4-[(E)-2-(1-ethyl-1H-imidazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetic acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (4-{4-[(4-[({4-[(E)-2-(1-ethyl-1H-imidazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl)phenyl)acetate (485 mg), 8N aqueous sodium hydroxide solution (1 mL), tetrahydrofuran (5 mL) and ethanol (5 mL) was heated under reflux for 30 min. After cooling, to the reaction mixture was added 1N hydrochloric acid (8 mL) and the mixture was left standing overnight. The precipitated crystals were collected by filtration and recrystallized from methanol-diethyl ether to give (4-{4-[(4-[({4-[(E)-2-(1-ethyl-1H-imidazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetic acid as colorless crystals (472 mg, yield 100%). melting point: 194-196° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling, to the reaction mixture
  4. waitthe mixture was left
  5. filtrationThe precipitated crystals were collected by filtration
  6. customrecrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-69ef60d0e9ab4407b20e72d8a7a32f44
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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