HCID 13176867, compound → HCID 13176868, compound

HRID 371424Notes

Reaction equation

HRID 371424 reaction equation
CS(O)(=O)=O.C([O:13][C:14]1[CH:35]=[CH:34][C:17]([C:18]([O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31](=[NH:33])[NH2:32])[CH:27]=3)[CH:22]=2)=[O:19])=[CH:16][CH:15]=1)C1C=CC=CC=1>[Pd].CN(C=O)C>[OH:13][C:14]1[CH:35]=[CH:34][C:17]([C:18]([O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31](=[NH:32])[NH2:33])[CH:27]=3)[CH:22]=2)=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 13176867HCID 13176867, compound

Product 1

HCID 13176868HCID 13176868, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To 50 ml of anhydrous DMF, were added 4.0 g of 6-amidino-2-naphthyl 4-benzyloxybenzoate methanesulfonate and 0.4 g of 10% Pd-C. The mixture was subjected to catalytic hydrogenation. After absorption of a stoichiometric amount of hydrogen, the reaction mixture was removed of Pd-C by filtration. After adding ethylether to the stirred filtrate, the precipitate was collected by filtration and recrystallized from a DMF-ethylether mixture to obtain 2.4 g of a white powder of 6-amidino-2-naphthyl 4-hydroxybenzoate methanesulfonate.

Workup

  1. customAfter absorption of a stoichiometric amount of hydrogen
  2. customthe reaction mixture was removed of Pd-C by filtration
  3. additionAfter adding ethylether to the stirred filtrate
  4. filtrationthe precipitate was collected by filtration
  5. customrecrystallized from a DMF-ethylether mixture

Sources & evidence

ORD record
ord-07bc86434d394640868c6bb33a76add7
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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