Methyl iodide → HCID 69818100, compound

Participants

Reaction Steps

To an ice-cooled solution of N-[4-[(2S)-3-acetoxy-2-[N-[(2S)-2-acetoxy-3-phenoxypropyl]-N-benzylamino]propyl]-phenyl]benzamide (107 mg) in tetrahydrofuran (1.1 ml) was added sodium hydride (60% in oil, 17 mg), and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added iodomethane (25 μl), and the mixture was stirred at room temperature for 1.5 hours before being partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was dissolved in methanol (1.1 ml)-1,4-dioxane (1.1 ml), then treated with 1N sodium hydroxide (0.5 ml) at room temperature for 1.5 hours. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give N-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]-amino]-3-hydroxypropyl]phenyl]-N-methylbenzamide (55 mg) as a white amorphous powder.

Provenance & Evidence