Potassium Carbonate → [4-Fluoro-2'-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid

HRID 456206Notes

Reaction equation

[CH3:1][C@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1.Br[C:35]1[CH:36]=[CH:37][C:38]([F:45])=[C:39]([CH2:41][C:42]([OH:44])=[O:43])[CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[F:45][C:38]1[CH:37]=[CH:36][C:35]([C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:23])([F:22])[F:24])=[CH:20][C:15]=2[CH2:14][N:3]2[C@@H:2]([CH3:1])[C@@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:5][C:4]2=[O:13])=[CH:40][C:39]=1[CH2:41][C:42]([OH:44])=[O:43]

Participants

Conditions

Temperature: 90 °C

Procedure

(4S,5R)-4-Methyl-5-phenyl-3-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-oxazolidin-2-one (0.080 g, 0.17 mmol), 5-bromo-2-fluorophenylacetic acid (0.061 g, 0.26 mmol), potassium carbonate (0.084 g, 0.61 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.021 g, 0.02 mmol) were combined in DME:H2O (2:1; 3 mL), and the mixture was purged with N2 for 5 minutes. The reaction was stirred under N2 at 90° C. overnight. After work-up with EtOAc and brine, the crude material was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound. M+H is 488.

Workup

customthe mixture was purged with N2 for 5 minutes
customAfter work-up with EtOAc and brine, the crude material was purified by silica gel chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-fd4b7ed0d84443efae10e23df2562847
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497381B2

Reaction notes

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