Ethanol → HCID 69422825, compound

HRID 350165Notes

Reaction equation

HRID 350165 reaction equation
[CH:1]([O:4][C:5]1[C:9]([CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[CH:8][N:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:29][C:30]=3[CH3:31])=[CH:20][CH:19]=2)[N:6]=1)([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1.C(O)C>Cl>[CH:1]([O:4][C:5]1[C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][N:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[O:29][C:30]=3[CH3:31])=[CH:20][CH:19]=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23024839HCID 23024839, compound

Product 1

HCID 69422825HCID 69422825, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of ethyl 3-[3-isopropoxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-yl]propionate (440 mg), 1 N aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred at room temperature for one hour, diluted with 1 N hydrochloric acid (5 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-isopropoxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionic acid was obtained (380 mg, yield: 91%). This was recrystallized from acetone-isopropyl ether. Melting point: 106–107° 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-da7ae151d6ad47e98dc283d612aea288
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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