Hydrochloric Acid → HCID 117759879, compound

HRID 1049563Notes

Reaction equation

HRID 1049563 reaction equation
[O:1]1CCCC1.B.[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:30]([CH:37]=[CH2:38])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:27]=[CH:28][CH:29]=2)=[CH:18][C:17]=1[CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41].C([O-])(=O)C.[Na+].OO.Cl>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:30]([CH2:37][CH2:38][OH:1])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:27]=[CH:28][CH:29]=2)=[CH:18][C:17]=1[CH2:39][C:40]([CH3:42])([CH3:41])[CH3:43]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 517045Sodium AcetateHCID 2723981Borane;tetrahydrofuranHCID 117759848HCID 117759848, compound

Product 1

HCID 117759879HCID 117759879, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, a solution (1.1 M, 5.2 mL) of tetrahydrofuran-borane in THF was added to a solution of ethyl 3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)pent-4-enoate (1.44 g) in THF (25 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added aqueous sodium acetate solution (3.0 M, 25 mL) and aqueous hydrogen peroxide (30%, 4.4 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added 1N hydrochloric acid at 0° C., the mixture was extracted with ethyl acetate. The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (440 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d9ad69a1dde5485babe1fe25b866950e
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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