4-Methylmorpholine → 6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N'-formylpyridazine-3-carbohydrazide

Participants

Reaction Steps

To a mixture of 6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid (1.4 mmol) from Step 1, formic hydrazide (107 mg, 1.8 mmol), EDCI (394 mg, 2.1 mmol), and 1-hydroxybenzotriazole hydrate (426 mg, 2.7 mmol) in N,N-dimethylformamide (15 mL) was added 4-methylmorpholine (0.45 mL, 4.1 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine prior to drying over magnesium sulfate. Filtration and removal of the volatiles under reduced pressure yielded titled compound as a glassy off-white amorphous solid, which was used without further purification.

Provenance & Evidence