Water → HCID 57709063, compound

HRID 546809Notes

Reaction equation

HRID 546809 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](B)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([C:19]([C:37]1[CH:42]=[CH:41][C:40](OS(C(F)(F)F)(=O)=O)=[C:39]([CH3:51])[CH:38]=1)([C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([CH2:34][CH3:35])([OH:33])[CH2:31][CH3:32])=[C:24]([CH3:36])[CH:23]=1)[CH2:20][CH3:21])[CH3:18].O>CN(C)C=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>[CH2:17]([C:19]([C:37]1[CH:42]=[CH:41][C:40]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)=[C:39]([CH3:51])[CH:38]=1)([C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([CH2:31][CH3:32])([OH:33])[CH2:34][CH3:35])=[C:24]([CH3:36])[CH:23]=1)[CH2:20][CH3:21])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57452669HCID 57452669, compoundHCID 178419145HCID 178419145, compound

Product 1

HCID 57709063HCID 57709063, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (6.8 mg, 0.0059 mmol), 3-carboxyphenylborane acid (6.8 mg, 0.0195 mmol) and potassium carbonate (13.4 mg, 97.5 μmol) were added to a solution of trifluoromethanesulfonic acid 4-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl ester (Example 1-(6); 10 mg, 0.0195 mmol) in N,N-dimethylformamide (0.5 mL) at room temperature, and then the mixture was stirred at 80° C. for five minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (chloroform/methanol=8/3, saturated with water) to give the title compound (5.6 mg, 60%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC (chloroform/methanol=8/3, saturated with water)

Sources & evidence

ORD record
ord-e9b0fea6b96a47f988a853634b94e7b7
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…