Indole → HCID 131723561, compound

Participants

Reaction Steps

Under N2 atmosphere, the Boc-DTrp-DPro-diisobutylamide was dissolved in 25 ml of CH2Cl2, 1 ml of methylsulfide and 0.5 ml of 1,2-ethanedithiol was added as scavenger in suppressing the indole alkylation of tryptophane. 10 ml of trifluoracetic acid was added dropwise while being stirred. The reaction mixture was stirred for 30 min. Volatiles were removed under vacuum and the residue was dissolved in 30 ml of CH2Cl2 and washed with 10 ml saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous sodium sulfate and filtered and the solvents were removed in vacuum. The residue was further purified by column chromatography (SiO2, CHCl2/MeOH, 85:15) to afford 0.55 mmol (78.5%) of compound (2) which was characterized by TLC and mass spectra, M+=411.5.

Provenance & Evidence