Hydrochloric Acid → HCID 178434839, compound

HRID 350159Notes

Reaction equation

HRID 350159 reaction equation
[OH:1][C:2]1[C:6]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=[CH:5][N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:17][CH:16]=2)[N:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[OH:1][C:2]1[C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][N:4]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[O:26][C:27]=3[CH3:28])=[CH:19][CH:20]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178471113HCID 178471113, compound

Product 1

HCID 178434839HCID 178434839, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl 3-[3-hydroxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (650 mg), 1 N aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (5 ml), and ethanol (10 ml) was stirred at room temperature for three hours, 1 N hydrochloric acid (5 ml) was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The obtained colorless crystals were collected by filtration, and 3-[3-hydroxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzyl]-1H-pyrazol-4-yl]propionic acid was obtained (560 mg, yield: 91%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 197–198° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-47804e138aec4c5184daf227d6132a4a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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