Synthesis of antiviral compound
A technology for compounds, reaction mixtures, applied in antiviral agents, drug combinations, organic chemistry, etc., which can solve problems such as limited practicality
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[0173] I. Synthesis of Starting Materials
[0174]
[0175] A. Cyclopropanation, Preparation 2
[0176] To a room temperature solution of DCM (1.5 L) and n-heptane (0.32 L) was added diethylzinc (800 mL, 1.0 M in n-heptane). The reaction mixture was cooled to 0 °C and a solution of compound 1 (45.0 g) in DCM (250 mL) was added over 10 min. When the addition was complete, the reaction mixture was cooled to -5 °C and chloroiodomethane (176 g) was added via syringe pump over 3.5 h. The reaction mixture was stirred at -5 °C for another 16 h and quenched by the slow addition (1 h) of 1 N aqueous HCl (1.4 L). After warming to 20 °C, the phases were separated and the aqueous layer was back extracted with DCM (0.5 L). The combined organic layers were washed with 10% aqueous NaCl (1.2 L), the phases were separated, and the organic layer was concentrated in vacuo to provide a crude oil, which was purified by silica gel flash chromatography (50% ethyl acetate / n-heptane). The desir...
Embodiment approach
[0238]
[0239] I. Cyclopropanation
[0240]
[0241] Cyclopropane to 12
[0242] Therefore, compound 1 (40 . 0g, 1.0eq), BnN(Me) 3 Cl (2.3 g, 0.07 eq), bromoform (45 mL, 3.0 eq) and DCM (280 mL) were added to the flask. The resulting solution was stirred at 33 °C and 50% sodium hydroxide solution (120 mL) was added within 1.5-2 h (internal temperature did not exceed 38 °C). The solution was aged at 33°C until the reaction was considered complete as determined by HPLC analysis. The contents of the flask were cooled to 22 °C, water (100 mL) was added, and the layer was allowed to stand for 2 h. The bottom aqueous layer was removed, and the upper organic layer was washed with 4M HCl (120 mL). The bottom organic layer was retained, and the upper aqueous layer was removed. The organic layer was then washed with water (80 mL). The lower organic layer was slurried with silica gel (12 g) for 1 h. The silica gel was filtered off and the waste cake was washed once with DC...
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