Hydrochloric Acid → HCID 69215670, compound

HRID 2221717Notes

Reaction equation

HRID 2221717 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[N:29]=[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:31][C:32]=3[CH3:33])=[C:22]([O:40][CH3:41])[CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[N:29]=[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:31][C:32]=3[CH3:33])=[C:22]([O:40][CH3:41])[CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10099149HCID 10099149, compound

Product 1

HCID 69215670HCID 69215670, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 1-benzyl-3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1H-pyrazole-4-carboxylate (1.80 g), tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (15 mL), and the mixture was heated under reflux for 4 hrs. 1N Hydrochloric acid (15 mL) and water were added to the reaction mixture, and the precipitated crystals were collected by filtration to give 1-benzyl-3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1H-pyrazole-4-carboxylic acid as crystals (1.70 g, yield 98%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 162-163° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-804bebfc71fe4a14a42e28c2d0b7aaa5
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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