Isovaleric Acid → HCID 13146230, compound

HRID 2413209Notes

Reaction equation

HRID 2413209 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].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>N1C=CC=CC=1>[C:1]([O:7][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:38](=[NH:39])[NH2:40])[CH:34]=2)[CH:29]=1)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 10430Isovaleric AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146230HCID 13146230, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.8 g of isovaleric 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 was collected by filtration, washed with a small volume of pyridine, then with 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 an ethanol-methanol (9:1) mixture to yield 2.0 g of colorless flaky crystals of 6-amidino-2-naphthyl isovalerate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with a small volume of pyridine
  4. dissolutionwith acetone, and dissolved 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 an ethanol-methanol (9:1) mixture

Sources & evidence

ORD record
ord-2228a5c58d92409bae6783548c5ad13b
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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