Methyl iodide → 2-oxo-3-tert-butoxycarbonylamino-5-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979315Notes

Reaction equation

HRID 1979315 reaction equation
CI.[C:3](=O)(O)[O-].[Na+].[O:8]=[C:9]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[NH:12][CH2:11][CH:10]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CO>[O:8]=[C:9]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]([CH3:3])[CH2:11][CH:10]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 154908313-Tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one

Product 1

HCID 212019472-oxo-3-tert-butoxycarbonylamino-5-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 66.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl iodide (1.4 ml) and sodium bicarbonate (630 mg) were added to a solution of 2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (832 mg) in methanol (20 ml), the mixture was refluxed for 2 days. The reaction mixture was concentrated under reduced pressure, Water (30 ml) was added to the residue and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodiun sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1), to thereby obtain 585 mg of the title compound (Yield: 66.9%) as brown amorphous.

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure, Water (30 ml)
  3. additionwas added to the residue
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodiun sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-fa2f0095448d432087e55018591f713d
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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