Potassium Carbonate → HCID 44206167, compound
Reaction equation
C[O:2][C:3](=[O:43])[CH2:4][C:5]1[CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=2[CH2:29][N:30]2[C@@H:34]([CH3:35])[C@@H:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:32][C:31]2=[O:42])[C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:10]=1.[C:44]1(B(O)O)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][C@H:34]1[C@@H:33]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[O:32][C:31](=[O:42])[N:30]1[CH2:29][C:20]1[CH:21]=[C:22]([C:25]([F:28])([F:26])[F:27])[CH:23]=[CH:24][C:19]=1[C:7]1[C:8]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:2])=[O:43])[CH:6]=1Participants
6
Conditions
- Temperature
- 90 °C
Procedure
[2′-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-6-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester (0.100 g, 0.16 mmol), phenylboronic acid (0.029 g, 0.24 mmol), potassium carbonate (0.055 g, 0.40 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.018 g, 0.02 mmol) were combined in DME (2 mL) and H2O (1 mL), and the mixture was purged with N2 for 10 minutes. The reaction was stirred at 90° C. for 5 hours, until no starting material was seen by analytical LCMS. The pH was adjusted to pH 7 with saturated aqueous NH4Cl, and the mixture was extracted with EtOAc. The crude material was purified by silica gel chromatography to give the title compound. M+H is 546.
Workup
- customH2O (1 mL), and the mixture was purged with N2 for 10 minutes
- extractionthe mixture was extracted with EtOAc
- customThe crude material was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-1c026f5b3971441784a051a117907f1f
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497381B2
Reaction notes
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