Butyric Acid → HCID 13146228, compound

HRID 2413208Notes

Reaction equation

HRID 2413208 reaction equation
[C:1]([OH:6])(=[O:5])[CH2:2][CH2:3][CH3:4].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:37](=[NH:39])[NH2:38])[CH:33]=2)[CH:28]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:6][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:37](=[NH:38])[NH2:39])[CH:33]=2)[CH:28]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146228HCID 13146228, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.6 g of n-butyric 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 methane-sulfonate was added to the mixture and further stirred overnight at room temperature. The precipitate was collected by filtration, washed successively with a small volume of pyridine, ethyl ether, and acetone, and dissolved in methanol at room temperature. The insolubles were collected by filtration and washed with a small volume of methanol. The filtrate and the washings were concentrated under reduced pressure and admixed with ethyl ether. The precipitated crystals were recrystallized from ethanol to obtain 1.8 g of colorless flaky crystals of 6-amidino-2-naphthyl butyrate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed successively with a small volume of pyridine, ethyl ether, and acetone
  4. dissolutiondissolved in methanol at room temperature
  5. filtrationThe insolubles were collected by filtration
  6. washwashed with a small volume of methanol
  7. concentrationThe filtrate and the washings were concentrated under reduced pressure
  8. customThe precipitated crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-358487df04df437896859e764f0836fc
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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