4-(N-t-butyloxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-3-(4-t-butylphenyl)-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one → 3-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-(N-ethoxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-2-methyl-2H-pyrazol-5-one

HRID 1740091Notes

Reaction equation

HRID 1740091 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][CH2:10][CH2:11][N:12]([CH3:40])[C:13]([C:15]1[C:19](=[O:20])[N:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[N:17]([CH3:29])[C:16]=1[C:30]1[CH:35]=[CH:34][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=1)=[O:14])=[O:7])(C)(C)[CH3:2]>S(=O)(=O)(O)O.C(O)C>[C:36]([C:33]1[CH:32]=[CH:31][C:30]([C:16]2[N:17]([CH3:29])[N:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[C:19](=[O:20])[C:15]=2[C:13]([N:12]([CH2:11][CH2:10][O:9][CH2:8][C:6]([O:5][CH2:1][CH3:2])=[O:7])[CH3:40])=[O:14])=[CH:35][CH:34]=1)([CH3:37])([CH3:38])[CH3:39]

Participants

4

Reactant 1

HCID 154355074-(N-t-butyloxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-3-(4-t-butylphenyl)-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one

Product 1

HCID 154355083-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-(N-ethoxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-2-methyl-2H-pyrazol-5-oneYield 51.5%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 900 mg of 4-(N-t-butyloxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-3-(4-t-butylphenyl)-1-(4-cyanophenyl)-2-methyl- 2H-pyrazol-5-one and 10 ml of ethanol, 4 drops of concentrated sulfuric acid was added, and the resulting reaction solution was refluxed under heating for 2.5 hours. After the ethanol was removed by evaporation under reduced pressure, water was added, and the reaction solution was extracted with chloroform. The extract was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The insolubles were filtered off, and the filtrate was concentrated. The resulting residue was recrystallized in chloroform-ether-hexane to give 440 mg of the title compound as colorless crystals.

Workup

  1. additionwas added
  2. customthe resulting reaction solution
  3. temperaturewas refluxed
  4. temperatureunder heating for 2.5 hours
  5. customAfter the ethanol was removed by evaporation under reduced pressure, water
  6. additionwas added
  7. extractionthe reaction solution was extracted with chloroform
  8. washThe extract was washed with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationThe insolubles were filtered off
  11. concentrationthe filtrate was concentrated
  12. customThe resulting residue was recrystallized in chloroform-ether-hexane

Sources & evidence

ORD record
ord-b7c58bdd46aa413dab30c2f11971c3a0
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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