Acetonitrile → HCID 18643651, compound

HRID 981389Notes

Reaction equation

HRID 981389 reaction equation
ON1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.C1(N=[C:18]=[N:19][CH:20]2[CH2:25]CCCC2)CCCCC1.[C:26]([O:30][C:31]([NH:33][C@H:34]([C:39]([OH:41])=O)[CH2:35][C:36](=[O:38])[NH2:37])=[O:32])([CH3:29])([CH3:28])[CH3:27].[C:42](#[N:44])[CH3:43]>>[C:26]([O:30][C:31]([NH:33][C@H:34]([C:39]([N:44]1[CH2:25][CH2:20][N:19]([CH2:18][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:43][CH2:42]1)=[O:41])[CH2:35][C:36](=[O:38])[NH2:37])=[O:32])([CH3:27])([CH3:28])[CH3:29]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

Product 1

HCID 18643651HCID 18643651, compound

Procedure

1-Hydroxybenztriazole (4.63 g) and dicyclohexylcarbodimide (5.32 g) were added to a solution (200 ml) of N-tert-butoxycarbonyl-L-asparagine (6.0 g) in acetonitrile at room temperature, followed by stirring for 2 hours. Insoluble matters were removed by filtration and to the filtrate was added a solution (200 ml) of 1-benzylpiperazine (4.54 g) in acetonitrile, followed by stirring for 12 hours at room temperature. Insoluble matters were removed by filtration and the filtrate was concentrated and extracted with ethyl acetate. The ethyl acetate extract was washed with saturated aqueous sodium hydrogencarbonate solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain a colorless crystal 1-(N-tert-butoxycarbonyl-L-asparaginyl)-4-benzylpiperazine (11.3 g).

Workup

  1. customInsoluble matters were removed by filtration and to the filtrate
  2. additionwas added a solution (200 ml) of 1-benzylpiperazine (4.54 g) in acetonitrile
  3. stirringby stirring for 12 hours at room temperature
  4. customInsoluble matters were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwas washed with saturated aqueous sodium hydrogencarbonate solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-e85ca8af11de453fb12dbfadeba244b1
Source dataset
uspto-grants-1991_02
Patent number
US04990614

Reaction notes

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