Reaktion #1137440

Reaktionsgleichung

NaOH

6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-((trimethylsilyl)ethynyl)phenyl)-1H-imidazo[4,5-b]pyridine

formic Acid

potassium hydrogen sulfate

→

title compound

(2R,3 S,5R)-5-((6-chloro-5-(4-ethynylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)-2-(hydroxy-methyl)tetrahydro-2H-pyran-3-ol

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 15 minutes at rt
2. 2
   Sonstigethe layers were separated
3. 3
   ExtraktionThe aqueous phase was extracted with EtOAc (×2)
4. 4
   WaschenThe combined organic extracts were washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe resulting crude product was purified by column chromatography on Biotage™ 25 g column
9. 9
   Waschenby eluting with 50% EtOAc in DCM

Vorschrift

6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-((trimethylsilyl)ethynyl)phenyl)-1H-imidazo[4,5-b]pyridine (220 mg, 0.319 mmol) was dissolved in formic Acid (4.5 ml, 117 mmol) and sat. potassium hydrogen sulfate (0.5 ml, 0.319 mmol). The mixture was stirred at rt for 1 h, and then diluted with EtOAc. Then 3 M NaOH was added until a pH of pH 14 was reached. The mixture was stirred for 15 minutes at rt and then the layers were separated. The aqueous phase was extracted with EtOAc (×2). The combined organic extracts were washed with brine and dried over Na2SO4, filtered and concentrated. The resulting crude product was purified by column chromatography on Biotage™ 25 g column by eluting with 50% EtOAc in DCM to yield the title compound. LC-MS: m/e=400.32 (M+H)+ (Rt 1.71/4 min).

Quelle