Isovaleric Acid → HCID 53855083, compound

HRID 1154575Notes

Reaction equation

HRID 1154575 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:33]=[CH:32][C:31]([CH:34]=[CH:35][C:36](=[NH:38])[NH2:37])=[CH:30][CH:29]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:7][C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][C:36](=[NH:37])[NH2:38])=[CH:30][CH:29]=1)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 10430Isovaleric AcidHCID 10868DicyclohexylcarbodiimideHCID 54417104HCID 54417104, compound

Product 1

HCID 53855083HCID 53855083, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 10 ml of dried pyridine, was dissolved 1.0 g of isovaleric acid. To the solution, while being cooled in ice, was added 2.5 g of DCC. After 30 minutes of stirring, 2.6 g of 4-(β-amidinoethenyl)phenol methanesulfonate was added and the mixture was stirred overnight at room temperature. The reaction mixture was removed of precipitated DCU by filtration and the DCU was washed with pyridine. Ethyl ether was added to the combined filtrate to precipitate a white solid substance which was collected by filtration, washed with ethyl ether, and recrystallized from ethanol to yield 1.7 g of colorless flaky crystals of 4-(β-amidinoethenyl)phenyl isovalerate methanesulfonate.

Workup

  1. temperatureTo the solution, while being cooled in ice
  2. stirringthe mixture was stirred overnight at room temperature
  3. customThe reaction mixture was removed of precipitated DCU by filtration
  4. washthe DCU was washed with pyridine
  5. additionEthyl ether was added to the combined filtrate
  6. customto precipitate a white solid substance which
  7. filtrationwas collected by filtration
  8. washwashed with ethyl ether
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cf3da72538d9453698e9de56281176fe
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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