Dicyclohexylcarbodiimide → HCID 54491518, compound

HRID 1154576Notes

Reaction equation

HRID 1154576 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:40]1[CH:45]=[CH:44][C:43]([CH:46]=[CH:47][C:48](=[NH:50])[NH2:49])=[CH:42][CH:41]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:40]1[CH:45]=[CH:44][C:43]([CH:46]=[CH:47][C:48](=[NH:49])[NH2:50])=[CH:42][CH:41]=1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 54417104HCID 54417104, compound

Product 1

HCID 54491518HCID 54491518, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4.5 g of 6-benzyloxycarbonylaminocaproic acid in 45 ml of dried pyridine, while being cooled in ice, was added 4.2 g of DCC. After 30 minutes of stirring, 4.4 g of 4-(β-amidinoethenyl)phenol methanesulfonate was added to the solution and stirred overnight at room temperature. The reaction mixture was freed from the precipitated DCU by filtration and the DCU was washed with pyridine. Ethyl ether was added to the combined filtrate to precipitate an oily substance. The oily substance was separated from the supernatant, washed a few times with ethyl ether, and dissolved in ethanol. Ethyl ether was added to the ethanol solution to precipitate a white solid substance which on recrystallization from an ethanol-ethyl ether mixture yielded 4.8 g of colorless granular crystals of 4-(β-amidinoethenyl)phenyl 6-benzyloxycarbonylaminocaproate methanesulfonate.

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe reaction mixture was freed from the precipitated DCU by filtration
  3. washthe DCU was washed with pyridine
  4. additionEthyl ether was added to the combined filtrate
  5. customto precipitate an oily substance
  6. customThe oily substance was separated from the supernatant
  7. washwashed a few times with ethyl ether
  8. dissolutiondissolved in ethanol
  9. additionEthyl ether was added to the ethanol solution
  10. customto precipitate a white solid substance which
  11. customon recrystallization from an ethanol-ethyl ether mixture

Sources & evidence

ORD record
ord-27520991254343059cf8be952f0bcb5a
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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