Dicyclohexylcarbodiimide → HCID 22398779, compound

HRID 1734111Notes

Reaction equation

HRID 1734111 reaction equation
[CH3:1][CH:2]([CH:6]([CH3:10])[C:7]([OH:9])=O)[C:3]([OH:5])=[O:4].[ClH:11].Cl.[NH2:13][CH2:14][C:15]1[O:19][C:18]([C:20]([O:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2C(=N)N)=[O:21])=[CH:17][CH:16]=1.C1CCC([N:42]=[C:43]=[N:44]C2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[ClH:11].[C:3]([CH:2]([CH3:1])[CH:6]([CH3:10])[C:7]([NH:13][CH2:14][C:15]1[O:19][C:18]([C:20]([O:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:43](=[NH:42])[NH2:44])[CH:29]=3)[CH:24]=2)=[O:21])=[CH:17][CH:16]=1)=[O:9])([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 118482,3-Dimethylsuccinic acidHCID 22398830HCID 22398830, compound

Product 1

HCID 22398779HCID 22398779, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 2.3 g of 2,3-dimethylsuccinic acid, 2.0 g of -amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride and 66 mg of DMAP was added 25 ml of pyridine, and the mixture was stirred while cooling with ice. After 10 minutes, 2.16 g of DCC was added and the mixture was stirred for 1 hour at 4°-8° C. and then for 2 hours at 16°-17° C. The precipitate was filtered off, the filtrate was added in small portions into 150 ml of ether and the mixture was stirred for 1 hour at room temperature. The precipitate was collected by filtration, then 60 ml of acetone was added thereto and the mixture was stirred for 3 hours. The precipitate was collected by filtration to obtain 1.3 g of the intended product.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was stirred for 1 hour at 4°-8° C.
  3. waitfor 2 hours at 16°-17° C
  4. filtrationThe precipitate was filtered off
  5. additionthe filtrate was added in small portions into 150 ml of ether
  6. stirringthe mixture was stirred for 1 hour at room temperature
  7. filtrationThe precipitate was collected by filtration
  8. addition60 ml of acetone was added
  9. stirringthe mixture was stirred for 3 hours
  10. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8c8d363858d04c899fbfd93e1df02fb9
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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