Pyridine → HCID 23103062, compound

HRID 1625600Notes

Reaction equation

HRID 1625600 reaction equation
[N:1]1[CH:6]=CC=[CH:3][CH:2]=1.[C:7]([Cl:17])(=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)(=[O:20])C>CN(C)C1C=CN=CC=1>[ClH:17].[C:7](=[O:16])([O:20][CH2:3][CH2:2][NH:1][CH3:6])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049Pyridine3×HCID 8857Ethyl Acetate3×HCID 10387Benzyl chloroformate3×

Product 1

HCID 23103062HCID 23103062, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a mixture of tert-butyl 2-hydroxyethyl (methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and benzyl chlorocarbonate (1.57 mL) was dropwise added. After stirring at room temperature for 2 hrs., pyridine (0.65 mL) and benzyl chlorocarbonate (1.28 mL) were added. After stirring at room temperature for 5 days, pyridine (0.81 mL) was added under ice-cooling and a solution (5 mL) of benzyl chlorocarbonate (1.43 mL) in ethyl acetate was dropwise added slowly. After stirring at room temperature for 2 hrs., ethyl acetate (50 mL) was added to the mixture, washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 2 hrs., diethylether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.99 g) as a white solid.

Workup

  1. additionwas dropwise added
  2. stirringAfter stirring at room temperature for 5 days
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for 2 hrs
  5. washwashed with water (50 mL)
  6. dry with materiala 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. additiona 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue
  9. stirringAfter stirring at room temperature for 2 hrs
  10. addition, diethylether (10 mL) was added
  11. filtrationthe precipitated solid was collected by filtration
  12. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-41dcf27dae0542dbbd819de2f922686f
Source dataset
uspto-grants-2014_07
Patent number
US08784885B2

Reaction notes

Loading…