Hydrazine hydrate (1:1) → 4-(t-butoxycarbonylamino-methyl)-phthalic Acid Dimethyl Ester

HRID 2080727Notes

Reaction equation

HRID 2080727 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[C:5](=[CH:10][C:11]([CH2:14][N:15]2[C:23](=[O:24])C3C(=CC=CC=3)C2=O)=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[OH2:27].NN>CO>[CH3:1][O:2][C:3](=[O:26])[C:4]1[C:5](=[CH:10][C:11]([CH2:14][NH:15][C:23]([O:24][C:4]([CH3:5])([CH3:13])[CH3:3])=[O:27])=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 669417474-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-phthalic Acid Dimethyl Ester

Product 1

HCID 669416434-(t-butoxycarbonylamino-methyl)-phthalic Acid Dimethyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (909 mg) obtained in Example 7-2 was suspended in methanol (22 ml). Hydrazine monohydrate (0.13 ml) was dropped in this suspension and the whole was refluxed under heating for 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and then the residue was subjected to extraction with chloroform. The organic layer was washed with water and then with a saturated saline solution, followed by drying with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was dissolved in DMF (15 ml) and added with triethylamine (0.54 ml) and di-t-butyldicarbonate (851 mg), followed by stirring at room temperature for 15 hours. After the solvent was distilled off, the residue was subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution and then dried with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (779 mg) as a yellow oily substance.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 4 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionthe residue was subjected to extraction with chloroform
  6. washThe organic layer was washed with water
  7. dry with materialby drying with anhydrous sodium sulfate
  8. customThe residue obtained
  9. distillationby distilling the solvent
  10. dissolutionoff was dissolved in DMF (15 ml)
  11. additionadded with triethylamine (0.54 ml) and di-t-butyldicarbonate (851 mg)
  12. distillationAfter the solvent was distilled off
  13. extractionthe residue was subjected to extraction with chloroform
  14. washThe organic layer was washed with water
  15. dry with materiala saturated saline solution and then dried with anhydrous sodium sulfate
  16. customThe residue obtained
  17. distillationby distilling the solvent
  18. customoff was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-348ff405256949698f518f769539503f
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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