Cesium acetate → HCID 178461781, compound

HRID 2277294Notes

Reaction equation

HRID 2277294 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH:3]=1.C([O-])(=[O:25])C.[Cs+]>CN(C=O)C>[OH:25][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 5152919Cesium acetateHCID 86731217tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamate

Product 1

HCID 178461781HCID 178461781, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl ((2S)-1-((4-chloro-5-nitropyridin-2-yl)oxy)propan-2-yl)carbamate (4.83 g), cesium acetate (6.99 g) and DMF (40 mL) was stirred at 80° C. for 1 hr. The mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (3.84 g).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate and water
  4. customthe organic layer was separated
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d487727b82e045aba3056def36654764
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

Loading…