Ethanol → HCID 69424018, compound

HRID 350161Notes

Reaction equation

HRID 350161 reaction equation
[CH3:1][O:2][C:3]1[C:7]([CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[CH:6][N:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[N:25]=[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:27][C:28]=3[CH3:29])=[CH:18][CH:17]=2)[N:4]=1.[OH-].[Na+].O1CCCC1.C(O)C>Cl>[CH3:1][O:2][C:3]1[C:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][N:5]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[N:25]=[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:27][C:28]=3[CH3:29])=[CH:20][CH:21]=2)[N:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23024998HCID 23024998, compound

Product 1

HCID 69424018HCID 69424018, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of ethyl 3-[3-methoxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-yl]propionate (380 mg), 1 N aqueous sodium hydroxide solution (2 ml), tetrahydrofuran (4 ml), and ethanol (4 ml) was stirred at room temperature for 2 hours, diluted with 1 N hydrochloric acid (2 ml), and 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-methoxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionic acid was obtained (319 mg, yield: 89%). This was recrystallized from ethanol-hexane. Melting point: 127–128° C.

Workup

  1. extractionextracted 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-1f450863c64e48ed865fd4390e51d8bd
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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