Hydrochloric Acid → 2-[3-[3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethloxy]phenyl]acetic acid

HRID 1294307Notes

Reaction equation

HRID 1294307 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([O:31]C)=[O:30])[CH:25]=[CH:26][CH:27]=2)[O:17][N:16]=1.[OH-].[Na+].O.Cl>CO.O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[CH:25]=[CH:26][CH:27]=2)[O:17][N:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68883771Methyl 2-[3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethoxy]phenyl]acetate

Product 1

HCID 688845692-[3-[3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethloxy]phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-[3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethoxy]phenyl]acetate (604 mg) was dissolved in methanol-tetrahydrofuran (1:1, 12 mL) and a 1N aqueous sodium hydroxide solution (3 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, 1N hydrochloric acid (3 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals of 2-[3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethloxy]phenyl]acetic acid. Recrystallization from ethanol-hexane gave colorless needle crystals (522 mg, 89%). melting point: 128-129° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-918e4e2e520147d69f4e6e5b7aeeb4ee
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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