4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → 1-(5-Methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-5-propyl-azepane-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Participants

Reaction Steps

The title compound from example 47 (55 mg, 0.13 mmol) was dissolved in dry DMF (5 mL), then solid KHCO3 (26 mg, 0.25 mmol) and 4-Bromomethyl-5-methyl-[1,3]dioxol-2-one (48 mg, 0.25 mmol, prepared as described in J. Alexander, et. al. J. Med. Chem, 1996, 39, 480-486) were added. The resulting mixture was stirred for 16 h, and the solvents were removed under reduced pressure, then the residue was purified by chromatography on silica with 5% MeOH/DCM followed by preparative HPLC to provide the title compound (47 mg, 68%) as a white solid.

Provenance & Evidence