Water → HCID 59139275, compound

HRID 2061105Notes

Reaction equation

HRID 2061105 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[C:6](=NNC(OC)=O)[CH3:7])[CH3:2].O.C(OCC)(=[O:28])C>CC(C)=O.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[C:6](=[O:28])[CH3:7])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 76656307HCID 76656307, compound2×

Product 1

HCID 59139275HCID 59139275, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 180AcetoneSolvent

Procedure

Titanium trichloride (10% solution in 20-30% HCl) was added to a solution of 3-(methoxycarbonylhydrazono)-2-(3-nitrophenylamino)butyric acid ethyl ester (compound 1c-51a) (5.0 g, 14.78 mmol) in acetone (50 mL), and the mixture was stirred at room temperature for 1 hour. Water was then added to the reaction mixture, extraction was performed with ethyl acetate, and the organic extract was washed with water and saturated saline. After drying over magnesium sulfate, it was concentrated under reduced pressure to yield a crude product, which was then purified by column chromatography to yield the title compound (3.75 g, 95%) as a yellow oil.

Workup

  1. extractionthe organic extract
  2. washwas washed with water and saturated saline
  3. dry with materialAfter drying over magnesium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customto yield a crude product, which
  6. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-fc707b66ea654962a1d1a3eb6f231602
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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