L-Pyroglutamic Acid → HCID 10300009, compound

Participants

Reaction Steps

To a stirred solution of pyroglutamic acid (400 mg, 3.1 mmol) in methylene chloride (6 mL), was added thionyl chloride (4 mL) along with a drop of pyridine at room temperature. The reaction mixture was allowed to stir for 2 h and concentrated. The residue was dissolved in 2 mL methylene chloride. To this stirred solution, was added the compound E of Example 2 (40 mg, 0.106 mmol) and diisopropylethylamine (0.5 mL, 3 mmol) in methylene chloride (5 mL). The mixture was allowed to stir for 16 h, and concentrated. The residue was dissolved in ethyl acetate (50 mL). The resultant solution was washed successively with 1N aqueous potassium bisulfate, saturated aqueous sodium bicarbonate and brine. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by preparative HPLC (aqueous methanol with 0.1% TFA) to give 15 mg of the title compound as a white solid. MS (M+NH4): 507.

Provenance & Evidence