Sodium Hydroxide → 3-(4-(3-Methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid

HRID 534861Notes

Reaction equation

HRID 534861 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[O:15][CH:16]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[O:15][CH:16]=2)[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66751235Methyl 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Product 1

HCID 667508253-(4-(3-Methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acidYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 45, 0.091 g, 0.290 mmol) and sodium hydroxide (0.50 mL, 1.0 M in water, 0.50 mmol) in methanol (5.0 mL) was stirred for 6 h at room temperature. After this time, the reaction mixture was quenched with 1.0 M hydrochloric acid (0.60 mL), diluted with ethyl acetate and separated. The organic layer was washed with water, and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, methylene chloride/methanol 49:1) to provide 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid (0.068 g, 75%) as a white solid.

Workup

  1. customAfter this time, the reaction mixture was quenched with 1.0 M hydrochloric acid (0.60 mL)
  2. additiondiluted with ethyl acetate
  3. customseparated
  4. washThe organic layer was washed with water, and saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography (silica gel, methylene chloride/methanol 49:1)

Sources & evidence

ORD record
ord-6adfae052a2b41129ac9442cf7edc52a
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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