Isovaleric Acid → HCID 13178433, compound

HRID 1589471Notes

Reaction equation

HRID 1589471 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]([C:34](=[NH:36])[NH2:35])=[CH:30][C:29]=1[O:37][CH3:38])(=O)=O>N1C=CC=CC=1>[C:1]([O:7][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[NH:35])[NH2:36])=[CH:30][C:29]=1[O:37][CH3:38])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 10430Isovaleric AcidHCID 10868DicyclohexylcarbodiimideHCID 54016649HCID 54016649, compound

Product 1

HCID 13178433HCID 13178433, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 40 ml of anhydrous pyridine, was dissolved 1.5 g of isovaleric acid. To the solution, while being cooled in ice, was added 3.7 g of DCC and the resulting mixture was stirred for 30 minutes. After addition of 3.9 g of 4-amidino-2-methoxyphenol methanesulfonate, the mixture was stirred overnight at room temperature. The precipitate which was formed was separated by filtration and washed with pyridine. Ethyl ether was added to the filtrate to precipitate colorless crystals. The crystals were washed with ethyl ether, dissolved in DMF, and recrystallized by adding ethyl ether. The crystals were further purified by recrystallizing from an ethanol-ethyl ether mixture to obtain 3.4 g of colorless flaky crystals of 4-amidino-2-methoxyphenyl isovalerate methanesulfonate.

Workup

  1. temperatureTo the solution, while being cooled in ice
  2. stirringthe mixture was stirred overnight at room temperature
  3. customThe precipitate which was formed
  4. customwas separated by filtration
  5. washwashed with pyridine
  6. additionEthyl ether was added to the filtrate
  7. customto precipitate colorless crystals
  8. washThe crystals were washed with ethyl ether
  9. dissolutiondissolved in DMF
  10. customrecrystallized
  11. additionby adding ethyl ether
  12. customThe crystals were further purified
  13. customby recrystallizing from an ethanol-ethyl ether mixture

Sources & evidence

ORD record
ord-ea680b1a5e2f43d992bcc647627f5114
Source dataset
uspto-grants-1986_02
Patent number
US04570006

Reaction notes

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