Dimethylformamide → HCID 178461781, compound

HRID 2277289Notes

Reaction equation

HRID 2277289 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>O>[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

5

Reactant 3

HCID 6228DimethylformamideHCID 5152919Cesium acetateHCID 86731217tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamate

Product 1

HCID 178461781HCID 178461781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl ((2S)-1-((4-chloro-5-nitropyridin-2-yl)oxy)propan-2-yl)carbamate (5.00 g), cesium acetate (7.23 g) and DMF (40 mL) was stirred at 0° C. for 10 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4228fff287164b6385d67bc972006e72
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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