N,N'-Dicyclohexylurea → HCID 86747151, compound

HRID 2255148Notes

Reaction equation

HRID 2255148 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([NH2:9])[C:7]#[N:8])[CH:2]=[CH2:3].[OH:10][N:11]=[C:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13](O)=[O:14].C1(N=C=NC2CCCCC2)CCCCC1.C1(NC(NC2CCCCC2)=O)CCCCC1>O1CCOCC1>[CH2:1]([O:4][CH2:5][CH:6]([NH:9][C:13](=[O:14])[C:12](=[N:11][OH:10])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:7]#[N:8])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 19739900HCID 19739900, compoundHCID 573586802-(Hydroxyimino)-4-methylpentanoic acid

Product 1

HCID 86747151HCID 86747151, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 750 ml of dioxane were dissolved 52 g of 3-allyloxy-2-aminopropionitrile, 40 g of α-hydroxyiminoisocaproic acid and 34.9 g of N-hdyroxysuccinimide. Thereto was added 59.7 g of N,N'-dicyclohexylcarbodiimide. The mixture was subjected to a reaction for 16 hours at room temperature. After completion of the reaction, N,N'-dicyclohexylurea was removed by filtration. The filtrate was concentrated to remove dioxane. The resulting residue was mixed with 800 ml of ethyl acetate. The mixture was washed with an aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (eluting solvent: 40% by volume of ethyl acetate-n-hexane) to obtain 67 g of 3-allyloxy-2-(α-hydroxyiminoisocaproylamino)propionitrile (Compound B-2) as white crystals.

Workup

  1. customThe mixture was subjected to a reaction for 16 hours at room temperature
  2. customwas removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customto remove dioxane
  5. additionThe resulting residue was mixed with 800 ml of ethyl acetate
  6. washThe mixture was washed with an aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed by evaporation
  9. customThe residue was purified by a silica gel column chromatography (eluting solvent: 40% by volume of ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-7e0c90d064aa460299f551d4f8dc37c4
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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