Benzyl Bromide → HCID 21201722, compound

HRID 1979306Notes

Reaction equation

HRID 1979306 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)(O)[O-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][CH:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 15490831HCID 15490831, compound

Product 1

HCID 21201722HCID 21201722, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (832 mg) was dissolved in methanol (20 ml), sodium bicarbonate (445 mg) and benzyl bromide (906 mg) were added, the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, the residue, after addition of water, was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, the crystals were washed with isopropyl ether, to thereby obtain 980 mg of the titled compound (Yield: 86.9%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue, after addition of water
  3. extractionwas extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. washthe crystals were washed with isopropyl ether

Sources & evidence

ORD record
ord-3b1823f5a2b346cab0c7be42af07efdb
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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