Dicyclohexylcarbodiimide → HCID 86747325, compound

HRID 1656880Notes

Reaction equation

HRID 1656880 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]([NH2:21])([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([OH:16])=[O:15])([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[O:37]1CCOCC1>ON1C(=O)CCC1=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]([NH2:21])([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([OH:16])=[O:15])([O-:3])=[O:2].[OH:3][N:1]1[C:14](=[O:16])[CH2:13][CH2:5][C:4]1=[O:37]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 312751,4-Dioxane2×HCID 19786233HCID 19786233, compound

Product 1

HCID 86747325HCID 86747325, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 80170N-HydroxysuccinimideSolvent

Procedure

2,4-dinitrophenyl-aminocaproic acid (300 mg) is dissolved in 6 ml of dioxane and N-hydroxysuccinimide, 120 mg in 4 ml of ethyl acetate, is added. N,N'-dicylohexylcarbodiimide, 200 mg in 2 ml of dioxane, is added, and the mixture is allowed to react for 3 h at room temperature. The precipitate which forms during the reaction is filtered off and the solution is evaporated to dryness under reduced pressure. The yellow residue is crystallized in boiling absolute ethanol. The yellow needles of the N-hydroxysuccinimide ester are collected and dried (Rf=0.59 by TLC in chloroform:ethyl acetate, 1:1 on silica gel).

Workup

  1. customto react for 3 h at room temperature
  2. filtrationis filtered off
  3. customthe solution is evaporated to dryness under reduced pressure
  4. customThe yellow residue is crystallized
  5. customThe yellow needles of the N-hydroxysuccinimide ester are collected
  6. dry with materialdried (Rf=0.59 by TLC in chloroform:ethyl acetate, 1:1 on silica gel)

Sources & evidence

ORD record
ord-a5ff6597c0354f35be526f49088fe128
Source dataset
uspto-grants-1993_10
Patent number
US05256395

Reaction notes

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