Diethyl Ether → HCID 13146233, compound

HRID 2413210Notes

Reaction equation

HRID 2413210 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:24][S:25]([O:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:41])[NH2:40])[CH:35]=2)[CH:30]=1)(=[O:27])=[O:26].C(OCC)C>N1C=CC=CC=1>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[C:1]([O:8][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:40])[NH2:41])[CH:35]=2)[CH:30]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146233HCID 13146233, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.1 g of caproic acid in 50 ml of anhydrous pyridine, while being cooled in ice, was added 4.4 g of DCC. After stirring for 30 minutes, 5.0 g of 6-amidino-2-naphthol methanesulfonate was added to the mixture and further stirred overnight at room temperature. The precipitate formed upon addition of ethyl ether to the reaction mixture was collected by filtration, washed with ethyl ether, dissolved in methanol at room temperature, and filtered to remove the insolubles. The filtrate was concentrated under reduced pressure and the residue was recrystallized from an ethanol-ether mixture to obtain 2.1 g of 6-amidino-2-naphthyl caproate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. filtrationwas collected by filtration
  3. washwashed with ethyl ether
  4. dissolutiondissolved in methanol at room temperature
  5. filtrationfiltered
  6. customto remove the insolubles
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was recrystallized from an ethanol-ether mixture

Sources & evidence

ORD record
ord-1923be65a72c48dcb8ac31b87abf967a
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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