Diethyl Ether → HCID 13146246, compound

HRID 2413217Notes

Reaction equation

HRID 2413217 reaction equation
[CH:1]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:38](=[NH:40])[NH2:39])[CH:34]=2)[CH:29]=1)(=O)=O.C(OCC)C>N1C=CC=CC=1>[CH:1]1([C:5]([O:7][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[C:33]([C:38](=[NH:39])[NH2:40])[CH:34]=3)[CH:29]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 19494Cyclobutanecarboxylic acidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146246HCID 13146246, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.8 g of cyclobutanecarboxylic acid in 50 ml of anhydrous pyridine, while being cooled in ice and stirred, was added 4.4 g of DCC. After 30 minutes, 5.0 g of 6-amidino-2-naphthol methanesulfonate was added to the mixture and the mixture was further stirred for 24 hours at room temperature. The precipitate formed on addition of ethyl ether was collected by filtration, dissolved in dimethylformamide, and filtered to remove the insolubles. Ethyl ether was added to the filtrate and the precipitate which was formed was collected by filtration and recrystallized from a dimethylformamide-ethyl ether mixture to yield 3.3 g of a white powder of 6-amidino-2-naphthyl cyclobutanecarboxylate methanesulfonate.

Workup

  1. stirringthe mixture was further stirred for 24 hours at room temperature
  2. filtrationwas collected by filtration
  3. dissolutiondissolved in dimethylformamide
  4. filtrationfiltered
  5. customto remove the insolubles
  6. additionEthyl ether was added to the filtrate
  7. customthe precipitate which was formed
  8. filtrationwas collected by filtration
  9. customrecrystallized from a dimethylformamide-ethyl ether mixture

Sources & evidence

ORD record
ord-3f2e94fa853a428eac7c0f7179e6c0f7
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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