HCID 66839062, compound → HCID 86628501, compound

HRID 546659Notes

Reaction equation

HRID 546659 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7].[H][H]>C(O)C.[C].[Pd]>[CH2:17]([CH:5]1[CH2:4][CH2:3][CH2:2][N:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]1=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 66839062HCID 66839062, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86628501HCID 86628501, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% palladium-carbon powder (50.36% aqueous, 1.92 g) was added to a solution of the (E)/(Z) mixture of tert-butyl N′-[5-chloro-2-(1-phenylmethylidene)pentanoyl]hydrazinecarboxylate obtained in the process of Example 12 in ethanol (20 mL), and the reaction solution was stirred in a hydrogen atmosphere at room temperature for 10 days. Thereafter, the reaction solution was filtered through celite and the solvent was evaporated under reduced pressure. DBU (0.598 mL) was added to a solution of the resulting residue in THF (50 mL) and the mixture was heated under reflux for 44 hours. Thereafter, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 727 mg of the title compound. The property values of the compound are as follows.

Workup

  1. filtrationThereafter, the reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. additionDBU (0.598 mL) was added to a solution of the resulting residue in THF (50 mL)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 44 hours
  6. customThereafter, the solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-e6a03d251ae84d478369f1654a75357d
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…