Dicyclohexylcarbodiimide → 3-Amino-N-[S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]propylamine

HRID 249573Notes

Reaction equation

HRID 249573 reaction equation
[CH2:1]([S:8][CH2:9][C@@H:10]([C:26](O)=[O:27])[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:30]1[C:34](=O)[CH2:33][CH2:32]C1=O.C1CCC([N:43]=C=NC2CCCCC2)CC1>CN(C=O)C>[NH2:43][CH:32]([C:26](=[O:27])[C@H:10]([CH2:9][S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:33][CH2:34][NH2:30]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 14969990S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine

Product 1

HCID 677883303-Amino-N-[S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]propylamineYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine (2.04 g) and N-hydroxysuccinimide (0.563 g) in DMF (5 ml), DCC (1.11 g) dissolved in DMF (5 ml) was added dropwise. The mixture was stirred for 0.5 hr. under ice cooling and for 0.5 hr. at room temperature, and filtered. To the filtrate, 1,3-diaminopropane (1.09 g) dissolved in DMF (30 ml) was added dropwise with stirring. The mixture was stirred for lhr and water was added to the mixture, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 1.6 g (69%) of the titled compound.

Workup

  1. additionwas added dropwise
  2. waitunder ice cooling and for 0.5 hr
  3. filtrationat room temperature, and filtered
  4. dissolutionTo the filtrate, 1,3-diaminopropane (1.09 g) dissolved in DMF (30 ml)
  5. additionwas added dropwise
  6. stirringwith stirring
  7. stirringThe mixture was stirred for lhr and water
  8. additionwas added to the mixture
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with water and saturated sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-a59226f9f9604a42b14f45336166eb61
Source dataset
uspto-grants-1993_05
Patent number
US05214181

Reaction notes

Loading…