Benzene → 6-Amidino-2-naphthyl 5-(3-methoxycarbonylpropionylaminomethyl)furan-2-carboxylate hydrochloride

HRID 1734109Notes

Reaction equation

HRID 1734109 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:23](=[NH:25])[NH2:24])[CH:19]=3)[CH:14]=2)=[O:11])=[CH:7][CH:6]=1.N1C=CC=CC=1.C1C=CC=CC=1.[CH3:38][O:39][C:40]([CH2:42][CH2:43][C:44]([Cl:46])=[O:45])=[O:41]>CN(C=O)C.CCOCC>[ClH:46].[CH3:38][O:39][C:40]([CH2:42][CH2:43][C:44]([NH:3][CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:23](=[NH:24])[NH2:25])[CH:19]=3)[CH:14]=2)=[O:11])=[CH:7][CH:6]=1)=[O:45])=[O:41]

Participants

7

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 223988156-Amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride

Product 1

HCID 223988166-Amidino-2-naphthyl 5-(3-methoxycarbonylpropionylaminomethyl)furan-2-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 18 g of 6-amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride in 380 ml of DMF was added 19.1 ml of pyridine and then, while cooling with ice, 20 ml of a benzene solution containing 7.5 ml of 3-methoxycarbonylpropionyl chloride was added dropwise thereto for 20 minutes. After stirring at room temperature for 2.5 hours, the reaction mixture was added to 2 l of ether while stirring and cooling with ice, and the mixture was stirred at the same temperature for 5 hours. The supernatant was decanted and 1.5 l of ether was further added and stirred at room temperature for 18 hours. The precipitate was collected by filtration, 800 ml of acetone was added thereto, the mixture was stirred at room temperature for 5 hours, and the crystals were collected by filtration to obtain 19.6 g of the intended product.

Workup

  1. additionwas added dropwise
  2. stirringwhile stirring
  3. temperaturecooling with ice
  4. stirringthe mixture was stirred at the same temperature for 5 hours
  5. customThe supernatant was decanted
  6. addition1.5 l of ether was further added
  7. stirringstirred at room temperature for 18 hours
  8. filtrationThe precipitate was collected by filtration, 800 ml of acetone
  9. additionwas added
  10. stirringthe mixture was stirred at room temperature for 5 hours
  11. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-ffdf86ec4dd8478b9bd4c0f2c6af4399
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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