Water → 3-(4-(3-Cyano-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]([CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[O:16][CH:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)#[N:2].[OH-].[Li+].O>>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[O:16][CH:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1)#[N:2]Participants
Procedure
A solution of methyl 3-(4-(3-cyano-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 46, 0.276 g, 0.851 mmol), lithium hydroxide (0.024 g, 1.00 mmol) and water (0.016 g, 0.889 mmol) was stirred at 0° C. for 4 h and then warmed to room temperature overnight. After this time, the reaction mixture was quenched with 1.0 M hydrochloric acid (1.0 mL), diluted with ethyl acetate and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by preparative HPLC (95% water-acetonitrile with 0.05% v/v trifluoroacetic acid/95% acetonitrile-water with 0.05% v/v trifluoroacetic acid 1:1, 15 mL/min) to provide 3-(4-(3-cyano-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid (0.035 g, 13%) as a white solid.
Workup
- customAfter this time, the reaction mixture was quenched with 1.0 M hydrochloric acid (1.0 mL)
- additiondiluted with ethyl acetate
- customseparated
- washThe organic layer was washed with saturated sodium chloride
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resultant residue was purified by preparative HPLC (95% water-acetonitrile with 0.05% v/v trifluoroacetic acid/95% acetonitrile-water with 0.05% v/v trifluoroacetic acid 1:1, 15 mL/min)
Sources & evidence
- ORD record
- ord-3fb4251178c94521b67543455cc84794
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853215B2
Reaction notes
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