Ethyl Acetate → HCID 23158124, compound

HRID 601683Notes

Reaction equation

HRID 601683 reaction equation
[CH:1]([N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]3[N:14]=[N:15][N:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[C:17]=3[CH3:18])[CH:10]=2)[C:5]1=[O:27])([CH3:3])[CH3:2].C([O-])(=[O:30])C.[Na+].O.C(=O)(O)O.C(OCC)(=O)C>C(O)(=O)C.BrBr>[CH:1]([N:4]1[C:12](=[O:30])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]3[N:14]=[N:15][N:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[C:17]=3[CH3:18])[CH:10]=2)[C:5]1=[O:27])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 15985251HCID 15985251, compoundHCID 21993411Carbonic acid--water (1/1)

Product 1

HCID 23158124HCID 23158124, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 176Acetic AcidSolvent

Procedure

37 mg of the compound obtained in Example 119 was dissolved in 2.0 ml of acetic acid, then 41 mg of sodium acetate and 3 drops of bromine were added and the mixture was stirred at room temperature for 20 min. After adding saturated hydrogen carbonate water and ethyl acetate, organic layer was separated, and dried with anhydrous sodium sulfate. The residues obtained by distilling out the solvents under reduced pressure were purified by thin-layer silicagel chromatography (hexane:ethyl acetate=50:50) to obtain 19.5 mg of the above compound as a white solid.

Workup

  1. customwas separated
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe residues obtained
  4. distillationby distilling out the solvents under reduced pressure
  5. customwere purified by thin-layer silicagel chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-d7b41dfbf8be47ea85b66cd32898e465
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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