Potassium Carbonate → Tert-butyl 3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzylcarbamate

HRID 2178301Notes

Reaction equation

HRID 2178301 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[N:32][CH:33]=1>C(#N)C.O>[CH3:18][O:17][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:2]=1[O:1][CH2:27][C:28]1[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15713917HCID 15713917, compoundHCID 534389575-(Chloromethyl)-2-methoxypyridine hydrochloride

Product 1

HCID 118114124Tert-butyl 3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzylcarbamateYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (22.44 g, 88.59 mmol) in acetonitrile (250 mL) was added potassium carbonate (30.61 g, 221.5 mmol) and 5-(chloromethyl)-2-methoxypyridine hydrochloride (18.33 g, 94.46 mmol). The resulting mixture was heated to reflux and stirred. After 23 h, the light green suspension was allowed to cool to room temperature and was diluted with water (600 mL), resulting in the formation of a precipitate. The solids were isolated by filtration and washed with water. The moist solids were dissolved in dichloromethane (300 mL), and a small amount of water separated and was removed. The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 31.92 g (96%) of tert-butyl 3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzylcarbamate as an off-white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. customresulting in the formation of a precipitate
  4. customThe solids were isolated by filtration
  5. washwashed with water
  6. dissolutionThe moist solids were dissolved in dichloromethane (300 mL)
  7. customa small amount of water separated
  8. customwas removed
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3acfe7501ca9470598f470eb681724c2
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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