Trifluoroacetic acid → 3-(4-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1,3-oxazol-5-yl)propanoic acid
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]=[CH:21][O:22][C:23]=2[CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]=[CH:21][O:22][C:23]=2[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]Participants
3
Procedure
A mixture of tert-butyl 3-(4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1,3-oxazol-5-yl)propanoate (Example 177, 0.60 g, 1.36 mmol) and trifluoroacetic acid (5.0 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was suspended in water. The mixture was adjusted to pH 4 with 10% NaHCO3 and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting white solid was triturated with hexane and ethyl acetate successively to give the title compound (0.40 g) as a white solid: mp 180-181° C.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting white solid was triturated with hexane and ethyl acetate successively
Sources & evidence
- ORD record
- ord-4cc5ed2467244b1696fcb603cfca9174
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853215B2
Reaction notes
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