Chlorotrimethylsilane → HCID 59263901, compound

Participants

Reaction Steps

Chlorotrimethylsilane (1.323 mL) was added to a cooled (0° C.) solution of benzyl 2-(cycloheptylamino)ethyl(2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate, prepared as in Example 23 step i) (1.260 g) and triethylamine (1.81 mL) in dichloromethane (35 mL). The reaction mixture was stirred at room temperature for 2 h then a solution of benzyl 3-chloro-3-oxopropyl(phenethyl)carbamate, prepared as in Example 5 step ii) (0.991 g) in dichloromethane (10 mL) was added. The reaction mixture was stirred at room temperature for 4 h then diluted with ethyl acetate and washed with 2M hydrochloric acid (×2) and saturated sodium hydrogen carbonate. The organic layer was separated, washed with water and saturated brine, dried over sodium sulphate, filtered and evaporated. The crude product was purified by flash silica chromatography (Biotage), elution gradient 1 to 6% methanol in dichloromethane. Fractions containing product were evaporated to dryness to afford the product as a yellow foam (1.416 g). The material was used in the next step directly.

Provenance & Evidence