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

Participants

Reaction Steps

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.

Provenance & Evidence