Dicyclohexylcarbodiimide → HCID 178499606, compound

HRID 1419249Notes

Reaction equation

HRID 1419249 reaction equation
[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.CS([O-])(=O)=O.[C:19]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[C:27](O)[CH:26]=[CH:25]2)(=[NH:21])[NH2:20].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CO.CN(C=O)C.N1C=CC=CC=1>[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:27]2[CH:26]=[CH:25][C:24]3[C:29](=[CH:30][CH:31]=[C:22]([C:19](=[NH:20])[NH2:21])[CH:23]=3)[C:28]=2[CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:10])=[CH:7][CH:6]=1

Participants

9

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 85257Methanesulfonate2×HCID 1363653376-Amidino-1-methoxycarbonylmethyl-2-naphtholHCID 178514393HCID 178514393, compound

Product 1

HCID 178499606HCID 178499606, compoundYield 25.9%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

170 Milliliters of anhydrous pyridine and 72 ml of DMF were added to 8.1 g of 4-aminoiminomethylaminobenzoic acid.methanesulfonate, 10.0 g of 6-amidino-1-methoxycarbonylmethyl-2-naphthol.methanesulfonate, 71.6 g of DCC and 170 mg of DMAP, followed by stirring for 2 hours under cooling with ice and 24 hours at room temperature. The precipitate was filtered and washed with a small amount of DMF. The filtrate and the wash liquid were combined and this was concentrated under reduced pressure. To the residue was added 50 ml of DMF, and the resulting solution was added dropwise to 700 ml of ether, followed by stirring for 24 hours under cooling with ice. The supernatant was decanted, and then to the residue was added 200 ml of acetone, followed by stirring for 1 hour under cooling with ice. The precipitate was collected by filtration to obtain a crude product. To the collected precipitate was added 300 ml of methanol to dissolve the precipitate. To the solution was added 2 g of active carbon, followed by stirring for 30 minutes at room temperature. Insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. To the residue was added 100 ml of methanol to dissolve the residue with heating. The resulting solution was added dropwise to 300 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 4.2 g of the desired product.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with a small amount of DMF
  3. concentrationthis was concentrated under reduced pressure
  4. additionTo the residue was added 50 ml of DMF
  5. additionthe resulting solution was added dropwise to 700 ml of ether
  6. stirringby stirring for 24 hours
  7. temperatureunder cooling with ice
  8. customThe supernatant was decanted
  9. additionto the residue was added 200 ml of acetone
  10. stirringby stirring for 1 hour
  11. temperatureunder cooling with ice
  12. filtrationThe precipitate was collected by filtration
  13. customto obtain a crude product
  14. dissolutionto dissolve the precipitate
  15. additionTo the solution was added 2 g of active carbon
  16. stirringby stirring for 30 minutes at room temperature
  17. filtrationInsoluble matter was filtered off
  18. concentrationthe filtrate was concentrated under reduced pressure
  19. additionTo the residue was added 100 ml of methanol
  20. dissolutionto dissolve the residue
  21. temperaturewith heating
  22. additionThe resulting solution was added dropwise to 300 ml of acetone
  23. stirringby stirring for 24 hours
  24. temperatureunder cooling with ice
  25. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-624f3aff8c354ff39d6c4e6dd782f341
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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