HCID 86632977, compound → HCID 16123879, compound

HRID 1686463Notes

Reaction equation

HRID 1686463 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH2:19][C:20]([OH:22])=[O:21])[CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=1.[CH3:36][Zn]C>O1CCOCC1.C1(C)C=CC=CC=1.[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:1][C:2]1[CH:26]=[C:25]([S:27]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)(=[O:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH2:19][C:20]([OH:22])=[O:21])[CH:8]=[C:9]([CH3:36])[CH:10]=1

Participants

6

Reactant 2

HCID 86632977HCID 86632977, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 16123879HCID 16123879, compound

Reagents, catalysts & solvents 3

HCID 178506421HCID 178506421, compoundCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by treating the product from step (ii) (0.25 g) in dry dioxane (10 ml) with bisdiphenylphosphinoferrocene palladium (0.02 g) and 2.0M dimethylzinc in toluene (0.40 ml). The mixture was heated to reflux for 3 h, partitioned between water and ethyl acetate, the organics separated, dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was dissolved in methanol (10 ml), 2M NaOH (10 ml) added and stirred at RT overnight. The mixture was diluted with water, extracted with ether (discarded). The aqueous layer was acidified with 2M HCl, extracted with ethyl acetate, dried (MgSO4) and evaporated under reduced pressure to an oil, which was purified by RPHPLC to give a white solid (0.085 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. custompartitioned between water and ethyl acetate
  4. dry with materialthe organics separated, dried (MgSO4)
  5. customevaporated under reduced pressure to an oil
  6. dissolutionThe oil was dissolved in methanol (10 ml)
  7. addition2M NaOH (10 ml) added
  8. additionThe mixture was diluted with water
  9. extractionextracted with ether (discarded)
  10. extractionextracted with ethyl acetate
  11. dry with materialdried (MgSO4)
  12. customevaporated under reduced pressure to an oil, which
  13. customwas purified by RPHPLC

Sources & evidence

ORD record
ord-7c99c5fff31d45da8e51c5df92561e45
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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