Dicyclohexylcarbodiimide → 5-Hydroxy-N-[S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]pentylamine

HRID 249575Notes

Reaction equation

HRID 249575 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.ON1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=O.C1CC[CH:40]([N:43]=C=NC2CCCCC2)CC1>CN(C=O)C>[OH:35][CH:34]([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]([CH3:23])([CH3:24])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:33][CH2:32][CH2:31][CH2:40][NH2:43]

Participants

5

Reactant 3

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

Product 1

HCID 677875515-Hydroxy-N-[S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]pentylamineYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of S-benzyl-N-(3-benzylthio-2,2-dimethyl-propionyl)-L-cysteine (4.18 g) and N-hydroxysuccinimide (1.15 g) in DMF (10 ml), DCC (2.06 g) dissolved in DMF (10 ml) was added dropwise under ice cooling and the mixture was stood overnight. The mixture was filtered and 5-aminopentanol (1.55 g) dissolved in DMF (30 ml) was added to the filtrate. The mixture was stirred for 3 hr. at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. Ethyl acetate layer was washed with saturated sodium bicarbonate solution, water and then saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 3.4 g (69%) of the titled compound.

Workup

  1. additionwas added dropwise under ice cooling
  2. filtrationThe mixture was filtered
  3. dissolution5-aminopentanol (1.55 g) dissolved in DMF (30 ml)
  4. additionwas added to the filtrate
  5. customat room temperature
  6. additionWater was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. washEthyl acetate layer was washed with saturated sodium bicarbonate solution, water
  9. dry with materialsaturated sodium chloride solution, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-6ac41542c0da4bd2a1f1fe1a6ca9fc5a
Source dataset
uspto-grants-1993_05
Patent number
US05214181

Reaction notes

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