tert-Butanol → tert-Butyl (2-cyanopyridin-4-yl)carbamate

HRID 1838243Notes

Reaction equation

HRID 1838243 reaction equation
C([N:3]([CH2:6]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])=CC=1.[C:25]([OH:29])([CH3:28])([CH3:27])[CH3:26].[C:30]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)C(O)=O)#[N:31]>O>[C:25]([O:29][C:6](=[O:15])[NH:3][C:34]1[CH:38]=[CH:39][N:40]=[C:32]([C:30]#[N:31])[CH:33]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27625132-Cyanoisonicotinic Acid

Product 1

HCID 22939607tert-Butyl (2-cyanopyridin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While stirring at room temperature, 1.8 ml of triethylamine and 2.8 ml of DPPA were added in that order to 100 ml of t-butanol solution containing 1.5 g of 2-cyanoisonicotinic acid, and the mixture was heated under refulx for 4 hours and 25 minutes. The reaction mixture was cooled to room temperature, mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatography, and 1.34 g of the title compound was obtained from ethyl acetate-hexane (1:2, v/v) eluate.

Workup

  1. temperaturethe mixture was heated under refulx for 4 hours and 25 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-d792eb831adb4ae8936f7104c890d60a
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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