Potassium Carbonate → HCID 117159185, compound

HRID 1477591Notes

Reaction equation

HRID 1477591 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][CH:7]([OH:16])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:7]2[CH2:6][NH:5][C:3](=[O:4])[CH2:2][O:16]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 117839900HCID 117839900, compound

Product 1

HCID 117159185HCID 117159185, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (16 mL) of 2-bromo-N-[3-(4-fluorophenyl)-2-hydroxypropyl]acetamide (1.00 g, 3.45 mmol) synthesized in Reference Synthesis Example 42, potassium carbonate (715 mg, 5.17 mmol) was added and the resultant solution was stirred at 80° C. for 2.5 hours. After completion of the reaction, the reaction solution was filtered with Celite and the filtered residue was washed with ethanol. The filtrate was concentrated under reduced pressure and chloroform was added to the concentrated filtrate, followed by concentrating the filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/20→ethyl acetate/methanol=20/1 (v/v)) to obtain the title compound (100 mg, yield 14%).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. filtrationthe reaction solution was filtered with Celite
  4. washthe filtered residue was washed with ethanol
  5. concentrationThe filtrate was concentrated under reduced pressure and chloroform
  6. additionwas added to the concentrated filtrate
  7. concentrationby concentrating the filtrate under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/20→ethyl acetate/methanol=20/1 (v/v))

Sources & evidence

ORD record
ord-1fdf78d6b30b4f80a6ed8034dde57db2
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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