Pyridine → HCID 178505334, compound

HRID 1154577Notes

Reaction equation

HRID 1154577 reaction equation
C1CCC([N:7]=[C:8]=[N:9][CH:10]2CC[CH2:13][CH2:12][CH2:11]2)CC1.[CH3:16][S:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29](=[NH:31])[NH2:30])=[CH:23][CH:22]=1)(=[O:19])=[O:18].C([O:34][CH2:35][CH3:36])C.[N:37]1C=CC=CC=1>>[CH3:16][S:17]([OH:20])(=[O:19])=[O:18].[CH3:16][S:17]([OH:20])(=[O:19])=[O:18].[NH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:36][C:35]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29](=[NH:31])[NH2:30])=[CH:23][CH:22]=1)=[O:34])[C:8]([NH2:7])=[NH:37]

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 54417104HCID 54417104, compound

Product 1

HCID 178505334HCID 178505334, compound

Procedure

To a solution of 2.1 g of 6-quanidinocaproic acid in 50 ml of dried pyridine, was added 3.1 g of DCC. After 30 minutes of stirring, 2.6 g of 4-(β-amidinoethenyl)phenol methanesulfonate was added and the mixture was stirred overnight. The insolubles were separated by filtration, suspended in DMF, and removed by filtration. Ethyl ether was added to the combined filtrate to precipitate an oily substance. The oily substance was separated, added to a saturated aqueous sodium bicarbonate solution and stirred to precipitate yellow crystals. The crystals were suspended in ethanol and admixed with methanesulfonic acid to form a clear solution. Ethyl ether was added to the solution and the precipitated crystals were collected by filtration and recrystallized from ethanol to obtain 1.8 g of 4-(β-amidinoethenyl)phenyl 6-guanidinocaproate dimethanesulfonate.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe insolubles were separated by filtration
  3. customremoved by filtration
  4. additionEthyl ether was added to the combined filtrate
  5. customto precipitate an oily substance
  6. customThe oily substance was separated
  7. additionadded to a saturated aqueous sodium bicarbonate solution
  8. stirringstirred
  9. customto precipitate yellow crystals
  10. customto form a clear solution
  11. filtrationthe precipitated crystals were collected by filtration
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d5ccca31d84d4d6482d19d4bb2008b3c
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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