Hydrochloric Acid → HCID 22930722, compound

HRID 1295296Notes

Reaction equation

HRID 1295296 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][C:8]([O-:10])=[O:9])[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:25][C:26]=3[CH3:27])=[CH:15][CH:14]=2)=[N:3]1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[O:25][C:26]=3[CH3:27])=[CH:17][CH:18]=2)=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86591674HCID 86591674, compound

Product 1

HCID 22930722HCID 22930722, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl [1-methyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyloxy]-1H-pyrazol-4-ylacetate (379 mg), 1N aqueous sodium hydroxide solution (2 ml), tetrahydrofuran (4 ml) and ethanol (4 ml) was stirred at room temperature for 2 hrs. 1N Hydrochloric acid (2 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were collected by filtration to give [1-methyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyloxy]-1H-pyrazol-4-yl]acetic acid (333 mg, yield 91%), which was then recrystallized from ethanol-hexane. melting point: 148–149° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-0268fcdecd75434b8e389e093e4278df
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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