Dicyclohexylcarbodiimide → HCID 178505335, compound

HRID 980021Notes

Reaction equation

HRID 980021 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH:6]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[O:22][C:21]([C:23]([OH:25])=[O:24])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[C:7]([NH2:9])=[NH:8].[CH3:26][S:27]([O:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:43])[NH2:42])[CH:37]=2)[CH:32]=1)(=[O:29])=[O:28].C1CCC(N=C=NC2CCCCC2)CC1>N1C=CC=CC=1>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[NH:6]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[O:22][C:21]([C:23]([O:25][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:42])[NH2:43])[CH:37]=4)[CH:32]=3)=[O:24])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[C:7]([NH2:9])=[NH:8]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 178505351HCID 178505351, compound

Product 1

HCID 178505335HCID 178505335, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2.9 g of 5-(p-guanidinophenylethyl)-furan-2-carboxylic acid methanesulfonate, 2.2 g of 6-amidino-2-naphthol methanesulfonate and 1.9 g of DCC was added 15 ml of anhydrous pyridine. The reaction mixture was stirred overnight at room temperature. The insolubles were filtered off and the filtrate was added to 100 ml of ethyl ether with stirring. Decantation is conducted to remove the ethyl ether. After repeating the procedure several times, the filtrate was dissolved in a small amount of methanol and the resulting solution was added to a saturated aqueous sodium hydrogencarbonate solution while stirring. The insolubles which were precipitated were collected by filtration and washed with water and acetone. The precipitate was suspended in a small amount of methanol and methanesulfonic acid was added to the resulting suspension. The insolubles were filtered off and the filtrate was added with stirring to 100 ml of ethyl ether. The ethyl ether was removed by decantation. After repeating the procedure several times, acetone was added to the filtrate. The mixture was stirred and decanted to remove the acetone. To the resulting mixture was added a small amount of ethanol and isopropanol and stirred. A pale yellow solid which was precipitated was collected by filtration to give 2.5 g of 6-amidino-2-naphthyl 5-(p-guanidinophenylethyl)-furan-2-carboxylate dimethanesulfonate.

Workup

  1. filtrationThe insolubles were filtered off
  2. additionthe filtrate was added to 100 ml of ethyl ether
  3. stirringwith stirring
  4. customto remove the ethyl ether
  5. dissolutionthe filtrate was dissolved in a small amount of methanol
  6. additionthe resulting solution was added to a saturated aqueous sodium hydrogencarbonate solution
  7. stirringwhile stirring
  8. customThe insolubles which were precipitated
  9. filtrationwere collected by filtration
  10. washwashed with water and acetone
  11. additionwas added to the resulting suspension
  12. filtrationThe insolubles were filtered off
  13. additionthe filtrate was added
  14. stirringwith stirring to 100 ml of ethyl ether
  15. customThe ethyl ether was removed by decantation
  16. additionwas added to the filtrate
  17. stirringThe mixture was stirred
  18. customdecanted
  19. customto remove the acetone
  20. additionTo the resulting mixture was added a small amount of ethanol and isopropanol
  21. stirringstirred
  22. customA pale yellow solid which was precipitated
  23. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-cbd9b0e1ba2d419d8ff3a7da633d0297
Source dataset
uspto-grants-1987_01
Patent number
US04634783

Reaction notes

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