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

HRID 534859Notes

Reaction equation

HRID 534859 reaction equation
[Cl: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>[Cl: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:9])[F:11])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66751004Methyl 3-(4-(3-chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Product 1

HCID 667511183-(4-(3-Chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-(4-(3-chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 36, 0.386 g, 1.16 mmol) in methanol (10.0 mL) was added sodium hydroxide (1.50 mL, 1.0 M in water, 1.50 mmol) at room temperature. After 16 h, the reaction was quenched with 1.0 M hydrochloric acid (1.70 mL), diluted with ethyl acetate, washed with water, and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was triturated with methylene chloride and hexanes to provide 3-(4-(3-chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid (0.316 g, 85%) as a white powder.

Workup

  1. customthe reaction was quenched with 1.0 M hydrochloric acid (1.70 mL)
  2. additiondiluted with ethyl acetate
  3. washwashed with water, and saturated sodium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with methylene chloride and hexanes

Sources & evidence

ORD record
ord-b95e314122654296999a4b842c7bea2a
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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