Dicyclohexylcarbodiimide → 2-Furancarboxylic acid, 5-methoxy-, 6-(aminoiminomethyl)-2-naphthalenyl ester, monomethanesulfonate

HRID 980020Notes

Reaction equation

HRID 980020 reaction equation
[CH3:1][O:2][C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.C1CCC(N=C=NC2CCCCC2)CC1.[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]>N1C=CC=CC=1>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[CH3:1][O:2][C:3]1[O:7][C:6]([C:8]([O:10][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:42])[NH2:43])[CH:37]=3)[CH:32]=2)=[O:9])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7711072-Furancarboxylicacid,5-methoxy-(9CI)HCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 211497772-Furancarboxylic acid, 5-methoxy-, 6-(aminoiminomethyl)-2-naphthalenyl ester, monomethanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml of dry pyridine was dissolved 1.4 g of 5-methoxy-furan-2-carboxylic acid. To the resulting solution was added 2.5 g of DCC and the reaction mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added with stirring and cooling in ice 2.8 g of 6-amidino-2-naphthol methanesulfonate. The reaction mixture was stirred overnight at room temperature. The precipitate was collected by filtration, washed with dry pyridine, added to DMF and stirred. The insolubles were filtered off and ethyl ether was added to the filtrate. The precipitate was collected by filtration and washed with acetone to obtain 2.7 g of 6-amidino-2-naphthyl 5-methoxy-furan-2-carboxylate methanesulfonate.

Workup

  1. additionTo the reaction mixture was added
  2. stirringwith stirring
  3. stirringThe reaction mixture was stirred overnight at room temperature
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with dry pyridine
  6. additionadded to DMF
  7. stirringstirred
  8. filtrationThe insolubles were filtered off
  9. additionethyl ether was added to the filtrate
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with acetone

Sources & evidence

ORD record
ord-6834421ff5a34401a947cc65f80287a3
Source dataset
uspto-grants-1987_01
Patent number
US04634783

Reaction notes

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