Dicyclohexylcarbodiimide → 2-Diazonio-1-[(2,5-dioxopyrrolidin-1-yl)oxy]ethen-1-olate

HRID 83573Notes

Reaction equation

HRID 83573 reaction equation
S([NH:11]/[N:12]=[CH:13]/[C:14]([OH:16])=[O:15])(C1C=CC(C)=CC=1)(=O)=O.O[N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[O:24]=[C:19]1[CH2:20][CH2:21][C:22](=[O:23])[N:18]1[O:16][C:14](=[O:15])[CH:13]=[N+:12]=[N-:11]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 9583234Glyoxylic acid, (p-tolylsulfonyl)hydrazone

Product 1

HCID 713461412-Diazonio-1-[(2,5-dioxopyrrolidin-1-yl)oxy]ethen-1-olateYield 53.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under argon atmosphere, to a solution of (E)-2-(2-tosylhydrazono)acetic acid (1.42 g) in 1,4-dioxane (14 ml) were sequentially added N-hydroxysuccinimide (677 mg) and dicyclohexylcarbodiimide (1.21 g) at room temperature, and the mixture was stirred for 17 hours. This reaction mixture was filtered through Celite, and eluted with 1,4-dioxane. This filtrate was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/diethyl ether=1/3) to give the titled compound (579 mg).

Workup

  1. customat room temperature
  2. filtrationThis reaction mixture was filtered through Celite
  3. washeluted with 1,4-dioxane
  4. concentrationThis filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/diethyl ether=1/3)

Sources & evidence

ORD record
ord-d044f6738ca74c368d6832413c49a219
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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