Succinic Acid → HCID 22398781, compound

HRID 1734105Notes

Reaction equation

HRID 1734105 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[ClH:9].Cl.[NH2:11][CH2:12][C:13]1[O:17][C:16]([C:18]([O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31](=[NH:33])[NH2:32])[CH:27]=3)[CH:22]=2)=[O:19])=[CH:15][CH:14]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[ClH:9].[C:4]([CH2:3][CH2:2][C:1]([NH:11][CH2:12][C:13]1[O:17][C:16]([C:18]([O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31](=[NH:32])[NH2:33])[CH:27]=3)[CH:22]=2)=[O:19])=[CH:15][CH:14]=1)=[O:8])([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 1110Succinic AcidHCID 10868DicyclohexylcarbodiimideHCID 223988156-Amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride

Product 1

HCID 22398781HCID 22398781, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 22.3 g of succinic acid, 24.0 g of 6-amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride and 790 mg of DMAP was added 240 ml of pyridine, and the mixture was stirred while cooling with ice. After 10 minutes, 25.9 g of DCC was added and the mixture was stirred for 3 hours while cooling with ice and then for 16 hours at room temperature. The precipitate was filtered off, and the filtrate was added in small portions into 2 l of ether and stirred at room temperature for 3 hours. After removing the supernatant by decantation, 1 l of acetone was added to the residue and stirred for 3 hours. The precipitate was collected by filtration to obtain 24.0 g of the intended product.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was stirred for 3 hours
  3. temperaturewhile cooling with ice
  4. waitfor 16 hours at room temperature
  5. filtrationThe precipitate was filtered off
  6. additionthe filtrate was added in small portions into 2 l of ether
  7. stirringstirred at room temperature for 3 hours
  8. customAfter removing the supernatant by decantation, 1 l of acetone
  9. additionwas added to the residue
  10. stirringstirred for 3 hours
  11. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-73e5994fbbe04c33ae53d8b71c9e862f
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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