Water → 3-Methyl-7-oxo-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxylic acid

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Reaction Steps

To a solution of H5IO6 (12.93 g, 56.71 mmol) in wet CH3CN (150 mL, 0.75% H2O v/v) at r.t. was added CrO3 (128 mg, 1.28 mmol). The mixture was stirred until complete dissolved was achieved. Into a 100-mL round-bottom flask, was placed wet acetonitrile (35 mL), (2S,5R)-2-(hydroxymethyl)-3-methyl-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 149, 740 mg, 3.30 mmol, 1.00 equiv) and it was cooled to 0° C., then the above oxidation solution (35 mL, 3.00 equiv) was added dropwise during 30 min at 0° C. The resulting solution was stirred for 1 h at 0° C. in a water/ice bath and monitor by TLC until the material was consumed completely. Then it was diluted with 200 mL of chloroform and 50 mL of citric acid solution (25%). Separating the organic layer and the organic layer was washed by 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.700 g crude of the title compound as yellow oil.

Provenance & Evidence