Trifluoroacetic acid → 4-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methylpyridin-3-yl}-3-methylbenzoic acid
Reaction equation
[F:1][C:2]([F:54])([F:53])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:33]5[CH:45]=[CH:44][C:36]([C:37]([O:39]C(C)(C)C)=[O:38])=[CH:35][C:34]=5[CH3:46])[CH:29]=[N:30][C:31]=4[CH3:32])=[CH:24][N:23]=[C:22]([N:47]4[CH2:50][CH:49]([F:51])[CH2:48]4)[N:21]=3)[C@H:14]2[CH3:52])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(O)(C(F)(F)F)=O>>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:33]5[CH:45]=[CH:44][C:36]([C:37]([OH:39])=[O:38])=[CH:35][C:34]=5[CH3:46])[CH:29]=[N:30][C:31]=4[CH3:32])=[CH:24][N:23]=[C:22]([N:47]4[CH2:50][CH:49]([F:51])[CH2:48]4)[N:21]=3)[C@H:14]2[CH3:52])[CH:4]=[C:3]([C:2]([F:54])([F:53])[F:1])[CH:8]=1Participants
3
Reactant 2
Product 1
Procedure
To a 25 mL round bottom flask was added tert-butyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methylpyridin-3-yl}-3-methylbenzoate (Step A, 40 mg, 0.053 mmol) and TFA (4 mL). The mixture was stirred at room temperature for 10 minutes. Volatiles were removed. The residue was purified on silica gel chromatography (0 to 100% acetone/hexane), affording the title compound as white solid. LCMS (M+H)+: 704.1. RTA IC50: 26 nM.
Workup
- customVolatiles were removed
- customThe residue was purified on silica gel chromatography (0 to 100% acetone/hexane)
Sources & evidence
- ORD record
- ord-d5017ff9bb97432ca2da5492b385bf86
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353101B2
Reaction notes
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