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Ertugliflozin
acetic anhydride
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
Conditions | Yield |
---|---|
With pyridine In toluene at 5 - 20℃; for 24.25h; Inert atmosphere; | 89% |
With pyridine In toluene at 5 - 20℃; for 24.25h; | 5.4% |
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
Ertugliflozin
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; for 0.25h; | |
With sodium methylate In methanol at 20℃; for 3.25h; Inert atmosphere; |
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
((1R,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)-phenyl)-2,3,4-trihydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl)methyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 0.25 h / 20 °C 2: pyridine / toluene / 8.28 h / -10 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 3.25 h / 20 °C / Inert atmosphere 2: pyridine / toluene / 19.1 h / -10 - 20 °C / Inert atmosphere View Scheme |
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.25 h / 20 °C 2.1: methanol; water; isopropyl alcohol / 40 - 60 °C / 30 Torr 2.2: 40 - 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 3.25 h / 20 °C / Inert atmosphere 2: water; isopropyl alcohol / 10 h / 40 - 80 °C / Inert atmosphere View Scheme |
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