Hydrochloric Acid → 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionic acid

HRID 350107Notes

Reaction equation

HRID 350107 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:33])=[C:5]([CH2:7][O:8][C:9]2[CH:32]=[CH:31][C:12]([CH2:13][N:14]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:15]3)=[CH:11][CH:10]=2)[N:6]=1.O.[OH-].[Li+].O1CCCC1.Cl>CO.O>[CH3:1][C:2]1[O:3][C:4]([CH3:33])=[C:5]([CH2:7][O:8][C:9]2[CH:32]=[CH:31][C:12]([CH2:13][N:14]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:16]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[N:15]3)=[CH:11][CH:10]=2)[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69427136methyl 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionate

Product 1

HCID 694223653-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionate (254 mg), lithium hydroxide monohydrate (69.9 mg), tetrahydrofuran (6 ml), water (4 ml) and methanol (4 ml) was stirred at room temperature for 2 hours, and 1N hydrochloric acid (1.7 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), then concentrated to yield 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionic acid (243 mg, yield: 99%) as an amorphous substance.

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

Sources & evidence

ORD record
ord-0e76b7f28951487083813ffb1a8386ee
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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