1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23060629, compound

HRID 750362Notes

Reaction equation

HRID 750362 reaction equation
[C:1]([C:9]1[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:10]=1[C:11]([N:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH2:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[Br:35][C:33]1[CH:34]=[C:9]2[C:10](=[CH:31][CH:32]=1)[C:11](=[O:12])[N:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:14]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[C:1]2[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 230608192-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamide

Product 1

HCID 23060629HCID 23060629, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

[Step 3] To a solution (40 ml) of 2-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamide (2.0 g) in toluene was added 1,8-diazabicyclo[5.4.0]undeca-7-ene (1.1 g), and the mixture was heated under reflux for 48 hrs. The reaction mixture was concentrated under reduced pressure. To the residue were added water and 10% hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization (THF-diisopropyl ether) to give the title compound (1.4 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 48 hrs
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue were added water and 10% hydrochloric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, 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 recrystallization (THF-diisopropyl ether)

Sources & evidence

ORD record
ord-3313ca07526c4cf0adf540abbac8e236
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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