Tert-Butyl nitrite → HCID 86756977, compound

HRID 1979341Notes

Reaction equation

HRID 1979341 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:7][CH2:6][C:5]1=[O:22].CC(C)([O-])C.[K+].[N:29](OC(C)(C)C)=[O:30]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:7][C:6](=[N:29][OH:30])[C:5]1=[O:22]

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 21201885HCID 21201885, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86756977HCID 86756977, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
10 °C

Procedure

Under argon atmosphere, 1-methoxymethyl-2-oxo-5-(2-fluorophenyl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (5.26 g) was dissolved in toluene (50 ml), the mixture was cooled on ice, potassium tert-butoxide (9.8 g) was added thereto at internal temperature 10° C., and stirred for 30 minutes under ice-cooling. tert-Butyl nitrite (5.0 g) was added thereto, the mixture was allowed to room temperature, and stirred for one hour and 30 minutes. Saturated brine was added to the reaction mixture, extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel NH-DM1020, produced by Fujisilicia Co. Ltd., chloroform:methanol=20:1), to thereby obtain 2.35 g of the titled compound as pale brown amorphous.

Workup

  1. additionwas added
  2. temperaturecooling
  3. customwas allowed to room temperature
  4. stirringstirred for one hour and 30 minutes
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was successively washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (silica gel NH-DM1020, produced by Fujisilicia Co. Ltd., chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-0a5a619cbf104aa98b3f4e23d11bedd4
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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