tert-Butyl acetate → HCID 66603844, Verbindung
Reaktionsgleichung
[I:1][C:2]1[C:7]([CH:8]([OH:13])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:14])[N:5]=[C:4]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:3]=12.C(O[C:26]([CH3:29])([CH3:28])[CH3:27])(=O)C.Cl(O)(=O)(=O)=O>>[I:1][C:2]1[C:7]([CH:8]([O:13][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:14])[N:5]=[C:4]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:3]=12Komponenten
4
Versuchsvorschrift
To a solution of methyl 2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-hydroxyacetate (2.1 g; 5.03 mmol) in tert-butyl acetate (15 mL; 112 mmol) under a nitrogen atmosphere was added perchloric acid 70% (0.342 mL; 5.52 mmol). The reaction was stirred at room temperature for 3 days and quenched by adding a saturated solution of sodium bicarbonate. The mixture was diluted with dichloromethane and the phases were separated. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethylacetate (1-40%) in heptane furnished 0.776 g (32%) of the title compound as a solid.
Aufarbeitung
- customquenched
- additionby adding a saturated solution of sodium bicarbonate
- additionThe mixture was diluted with dichloromethane
- customthe phases were separated
- dry with materialThe organic layer was dried over sodium sulphate
- concentrationconcentrated under reduced pressure
- customPurification by flash-chromatography on silica gel using a gradient of ethylacetate (1-40%) in heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-a9fabb154db14636a1c7894625c3781d
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08785638B2
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