Hydrochloric Acid → HCID 22398794, compound

HRID 1734100Notes

Reaction equation

HRID 1734100 reaction equation
[ClH:1].C[O:3][C:4]([CH2:6][C:7]1[CH:37]=[CH:36][C:10]([C:11]([NH:13][CH2:14][C:15]2[O:19][C:18]([C:20]([O:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:33](=[NH:35])[NH2:34])[CH:29]=4)[CH:24]=3)=[O:21])=[CH:17][CH:16]=2)=[O:12])=[CH:9][CH:8]=1)=[O:5].Cl>C(O)(=O)C>[ClH:1].[C:4]([CH2:6][C:7]1[CH:37]=[CH:36][C:10]([C:11]([NH:13][CH2:14][C:15]2[O:19][C:18]([C:20]([O:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:33](=[NH:34])[NH2:35])[CH:29]=4)[CH:24]=3)=[O:21])=[CH:17][CH:16]=2)=[O:12])=[CH:9][CH:8]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22398814HCID 22398814, compound

Product 1

HCID 22398794HCID 22398794, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 3 g of 6-amidino-2-naphthyl 5-(4-methoxycarbonylmethylbenzoylaminomethyl)furan-2-carboxylate hydrochloride was added 60 ml of acetic acid, and hydrogen chloride gas was passed into the mixture until saturation while cooling with ice and stirring. Thereafter the mixture was stirred for 48 hours at 50° C. and then cooled with ice. The precipitate was collected by filtration and washed with 100 ml of acetone. The crystals were dissolved in 40 ml of DMF, then 1 g of active carbon was added to the solution and stirred for 1 hour while cooling with ice. Thereafter, the insolubles were removed by filtration, 90 ml of acetone was added to the filtrate and stirred for 18 hours at room temperature. The precipitate was collected by filtration and washed with 50 ml of acetone to obtain 1.3 g of the intended product.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThereafter the mixture was stirred for 48 hours at 50° C.
  3. temperaturecooled with ice
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with 100 ml of acetone
  6. dissolutionThe crystals were dissolved in 40 ml of DMF
  7. addition1 g of active carbon was added to the solution
  8. stirringstirred for 1 hour
  9. temperaturewhile cooling with ice
  10. customThereafter, the insolubles were removed by filtration, 90 ml of acetone
  11. additionwas added to the filtrate
  12. stirringstirred for 18 hours at room temperature
  13. filtrationThe precipitate was collected by filtration
  14. washwashed with 50 ml of acetone

Sources & evidence

ORD record
ord-655e8e50456848d8bd76bebb67092658
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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