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Dimethylformamide → 6-Amidino-2-naphthyl 5-(3-t-butoxycarbonylmethylcarbamoylpropionylaminomethyl)furan-2-carboxylate hydrochloride

HRID 1734110
Notes
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Reaction equation

HRID 1734110 reaction equation
[ClH:1].[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].Cl.[C:12]([CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21]1[O:25][C:24]([C:26]([O:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:41])[NH2:40])[CH:35]=3)[CH:30]=2)=[O:27])=[CH:23][CH:22]=1)=[O:18])(O)=[O:13].CN(C=O)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[ClH:1].[C:2]([O:6][C:7]([CH2:8][NH:9][C:12]([CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21]1[O:25][C:24]([C:26]([O:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:40])[NH2:41])[CH:35]=3)[CH:30]=2)=[O:27])=[CH:23][CH:22]=1)=[O:18])=[O:13])=[O:10])([CH3:5])([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 22398781HCID 22398781, compound

Product 1

HCID 223987626-Amidino-2-naphthyl 5-(3-t-butoxycarbonylmethylcarbamoylpropionylaminomethyl)furan-2-carboxylate hydrochlorideYield 74.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 0.75 g of glycine t-butyl ester hydrochloride, 0.15 g of DMAP and 1.5 g of 6-amidino-2-naphthyl 5-(3-carboxypropionylaminomethyl)furan-2-carboxylate hydrochloride were added 20 ml of DMF and 1 ml of pyridine, and the mixture was stirred while cooling with ice. After 10 minutes, 0.9 g of DCC was added thereto, and the mixture was stirred for 3 hours while cooling with ice and then for 24 hours at room temperature. The precipitate was filtered off, the filtrate was added in small portions to 300 ml of ether, and the mixture was stirred at room temperature for 3 hours. The supernatant was decanted, then 200 ml of ether was added to the residue and stirred at room temperature for 19 hours. The precipitate was collected by filtration, then dissolved in 15 ml of methanol, 0.4 g of active carbon was added thereto and the mixture was stirred for 15 minutes while cooling with ice. The insoluble was filtered off, the filtrate was added to 200 ml of ether and the mixture was stirred for 5 hours while cooling with ice. The precipitate was collected by filtration to obtain 1.4 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 24 hours at room temperature
  5. filtrationThe precipitate was filtered off
  6. additionthe filtrate was added in small portions to 300 ml of ether
  7. stirringthe mixture was stirred at room temperature for 3 hours
  8. customThe supernatant was decanted
  9. addition200 ml of ether was added to the residue
  10. stirringstirred at room temperature for 19 hours
  11. filtrationThe precipitate was collected by filtration
  12. dissolutiondissolved in 15 ml of methanol
  13. addition0.4 g of active carbon was added
  14. stirringthe mixture was stirred for 15 minutes
  15. temperaturewhile cooling with ice
  16. filtrationThe insoluble was filtered off
  17. additionthe filtrate was added to 200 ml of ether
  18. stirringthe mixture was stirred for 5 hours
  19. temperaturewhile cooling with ice
  20. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9bd261b74ea345ceb600547733a07a12
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05532267

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes