Pyridine → HCID 13176887, compound

HRID 371426

Reaction equation

HRID 371426 reaction equation
N1C=CC=CC=1.[CH2:7]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:48]1[CH:57]=[CH:56][C:55]2[C:50](=[CH:51][CH:52]=[C:53]([C:58](=[NH:60])[NH2:59])[CH:54]=2)[CH:49]=1)(=O)=O>C(OCC)C>[CH2:7]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][C:48]2[CH:57]=[CH:56][C:55]3[C:50](=[CH:51][CH:52]=[C:53]([C:58](=[NH:59])[NH2:60])[CH:54]=3)[CH:49]=2)=[O:24])=[CH:26][CH:27]=1)=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 14799974-((((Benzyloxy)carbonyl)amino)methyl)benzoic acidHCID 13050560HCID 13050560, compound

Product 1

HCID 13176887HCID 13176887, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 50 ml of dried pyridine, were added 5.1 g of 4-benzyloxycarbonylaminomethylbenzoic acid and 4.4 g of DCC. The mixture was stirred under cooling in ice for 30 minutes, admixed with 5.0 g of 6-amidino-2-naphthol methanesulfonate and stirred for one hour under cooling in ice, then overnight at room temperature. The reaction mixture was filtered* and the filtrate was mixed with ethyl ether. The precipitate which was formed was collected by filtration and recrystallized from a DMF-ethanol mixture to obtain 3.8 g of a white powder of a white powder of 6-amidino-2-naphthyl 4-benzyloxycarbonylaminomethylbenzoate methanesulfonate.

Workup

  1. temperatureunder cooling in ice for 30 minutes
  2. stirringstirred for one hour
  3. temperatureunder cooling in ice
  4. customovernight
  5. customat room temperature
  6. customThe precipitate which was formed
  7. filtrationwas collected by filtration
  8. customrecrystallized from a DMF-ethanol mixture

Sources & evidence

ORD record
ord-9e5fc2c2395f4db097b15096d444a484
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Linked notes

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