Acetic Acid → HCID 22398787, compound

HRID 1734099Notes

Reaction equation

HRID 1734099 reaction equation
[ClH:1].C([O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][CH2:19][C:20]2[O:24][C:23]([C:25]([O:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[C:33]([C:38](=[NH:40])[NH2:39])[CH:34]=4)[CH:29]=3)=[O:26])=[CH:22][CH:21]=2)=[O:17])=[CH:11][CH:10]=1)=[O:8])(C)(C)C.C(O)(=O)C.Cl>O>[ClH:1].[C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH:18][CH2:19][C:20]2[O:24][C:23]([C:25]([O:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[C:33]([C:38](=[NH:39])[NH2:40])[CH:34]=4)[CH:29]=3)=[O:26])=[CH:22][CH:21]=2)=[O:17])=[CH:13][CH:14]=1)([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22398770HCID 22398770, compound

Product 1

HCID 22398787HCID 22398787, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.4 g of 6-amidino-2-naphthyl 5-(4-t-butoxycarbonylphenylacetylaminomethyl)furan-2-carboxylate hydrochloride was added 8 ml of acetic acid, and hydrogen chloride gas was passed into the mixture for 2 hours while stirring and cooling with ice. The mixture was further stirred for 2.5 hours with water-cooling, the precipitate was collected by filtration and washed twice with 20 ml of acetone. The crystals were dissolved in 20 ml of DMF, then 1 g of active carbon was added to the solution and stirred for 30 minutes while cooling with ice. The insolubles were removed by filtration, the filtrate was added to 250 ml of acetone and stirred for 2 hours at room temperature. The precipitate was collected by filtration to obtain 3.2 g of the intended product.

Workup

  1. temperaturecooling with ice
  2. temperaturecooling
  3. filtrationthe precipitate was collected by filtration
  4. washwashed twice with 20 ml of acetone
  5. dissolutionThe crystals were dissolved in 20 ml of DMF
  6. addition1 g of active carbon was added to the solution
  7. stirringstirred for 30 minutes
  8. temperaturewhile cooling with ice
  9. customThe insolubles were removed by filtration
  10. additionthe filtrate was added to 250 ml of acetone
  11. stirringstirred for 2 hours at room temperature
  12. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a03b87545e8045728ee2bc80ec2cb880
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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