Cesium carbonate → 4-Benzyl-3-{2-[5-(4-fluoro-2-trifluoromethyl-benzyloxy)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one

HRID 599130Notes

Reaction equation

HRID 599130 reaction equation
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:37])[CH:15]([C:20]1[CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH:23]=[C:24]([OH:26])[CH:25]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=1[C:47]([F:50])([F:49])[F:48].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:37])[CH:15]([C:20]1[CH:21]=[C:22]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:36])[F:35])=[CH:31][CH:32]=2)[CH:23]=[C:24]([O:26][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=2[C:47]([F:49])([F:48])[F:50])[CH:25]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27375764-Fluoro-2-(trifluoromethyl)benzyl bromideHCID 666982624-Benzyl-3-[2-(5-hydroxy-4'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoyl]-oxazolidin-2-one

Product 1

HCID 765878014-Benzyl-3-{2-[5-(4-fluoro-2-trifluoromethyl-benzyloxy)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-benzyl-3-[2-(5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoyl]-oxazolidin-2-one (as prepared in Example 1, step (k))(0.400 g, 0.78 mmol) in acetonitrile (3.9 mL) was added 1-bromomethyl-4-fluoro-2-trifluoromethyl-benzene (0.181 mL, 1.17 mmol) and Cs2CO3 (0.508 g, 1.56 mmol). The resulting white suspension was stirred at room temperature for 1 h. The white solid was filtered off and the solvent was removed in vacuo to obtain relatively pure 4-benzyl-3-{2-[5-(4-fluoro-2-trifluoromethyl-benzyloxy)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one.

Workup

  1. filtrationThe white solid was filtered off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8616e1b4583744a2a922a917dfd9ea14
Source dataset
uspto-grants-2011_03
Patent number
US07897643B2

Reaction notes

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