Ethanol → HCID 131735471, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL roundbottom flask with stirbar was charged with sodium ethanolate, 21 wt % in ethanol (14 mL, 37.6 mmol), sealed and cooled to −20° C. under nitrogen. A mixture of Example 99A (6.38 g, 25.01 mmol) and ethyl 2-azidoacetate (10 g, 77 mmol) were added dropwise over 15 minutes. The solution was stirred for 3.5 hours, then poured into a separatory funnel and extracted from 100 mL water with 3×100 mL ether. The combined organics were washed with saturated aqueous sodium chloride, dried over magnesium sulfate. After filtration and solvent removal the residues were chromatographed on a 60 g silica cartridge eluting with 0-10-100% ethyl acetate/heptane to provide 2.56 g (28%) of the title compound.

Provenance & Evidence