Triethylamine → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-methoxyacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

To a suspension of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-amino-tetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride (0.500 g, 1.31 mmol) in CH2Cl2 (20 mL) was added triethylamine (0.544 mL, 3.915 mmol), followed by 2-methoxyacetyl chloride (0.13 mL, 1.44 mmol). The reaction was stirred at room temperature for 18 h. The reaction mixture was washed once with saturated aqueous NaHCO3 (3 mL) and once with brine (3 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel (5:1 EtOAc:hexanes) afforded (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-methoxyacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white solid (0.380 g, 70% yield).

1. washThe reaction mixture was washed once with saturated aqueous NaHCO3 (3 mL) and once with brine (3 mL)
2. dry with materialThe organic layer was dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customPurification of the crude material by flash chromatography on silica gel (5:1 EtOAc:hexanes)

ORD-Eintrag

ord-1540d4933d31490abea3187e3f56e044

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08334310B2