Sodium Carbonate → (4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-methoxy-1,1'-biphenyl-4-yl)acetic acid

HRID 2076621Notes

Reaction equation

HRID 2076621 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C:21]2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:46][C:47]1[C:59]([C:60]([F:63])([F:62])[F:61])=[C:58](COC2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)[CH:57]=[CH:56][C:48]=1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50].[CH3:81][O:82][C:83]1[CH:84]=[C:85]([CH2:97][C:98]([O:100]C)=[O:99])[CH:86]=[CH:87][C:88]=1OS(C(F)(F)F)(=O)=O>C1(C)C(CCO)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:52]([O:51][C:49]([C:48]1[C:47]([OH:46])=[C:59]([C:60]([F:62])([F:61])[F:63])[CH:58]=[CH:57][C:56]=1[CH2:21][O:20][C:15]1[CH:16]=[CH:17][C:18]([C:88]2[CH:87]=[CH:86][C:85]([CH2:97][C:98]([OH:100])=[O:99])=[CH:84][C:83]=2[O:82][CH3:81])=[CH:19][CH:14]=1)=[O:50])([CH3:55])([CH3:53])[CH3:54]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 67119177Tert-butyl 2-hydroxy-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoateHCID 86617406Methyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate

Product 1

HCID 67119202(4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-methoxy-1,1'-biphenyl-4-yl)acetic acidYield 201.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 882672-Methylphenethyl alcoholSolvent

Conditions

Temperature
100 °C

Procedure

After a 2M aqueous sodium carbonate solution (0.5 ml), tris(dibenzylideneacetone)dipalladium (0) (18 mg, 0.02 mmol) and bis(2-diphenylphosphinophenyl)ether (DPEphos) (22 mg, 0.04 mmol) were added to a solution of tert-butyl 2-hydroxy-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (100 mg, 0.20 mmol) obtained in Example (22-4) and methyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate (79 mg, 0.24 mmol) obtained in Example (22-5) in a mixture of toluene-ethanol (6:1, 3.5 ml), the mixture was stirred at 100° C. for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and extracted with ethyl acetate (three times). The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The compound obtained by removing the solvent under reduced pressure was treated according to a method similar to Example (17-4) to give the title compound as a pale yellow powder (43 mg, yield: 40%).

Workup

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate (three times)
  3. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe compound obtained
  6. customby removing the solvent under reduced pressure
  7. additionwas treated

Sources & evidence

ORD record
ord-db5652859a7c4653bc76f7e16eadb3a5
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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