Acetic Anhydride → HCID 90203919, compound

Participants

Reaction Steps

To a solution of (Z)-3-(benzyloxy)-2-(1,1-dimethylethylsulfinamido)-N′-hydroxy-2-methylpropanimidamide (Example 112b, 1.25 g, 3.82 mmol) in dry DMF (25 ml) was added potassium carbonate (633 mg, 4.58 mmol) followed by addition of acetic anhydride (390 mg, 360 uL, 3.82 mmol). The reaction mixture was stirred at room temperature for 1 hour and was then stirred at 120° C. for 2 hours. DMF was removed in vacuo and the residue was dissolved in ethyl acetate which was extracted with a 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (1.20 g, purity: 80%, 72%) as a light yellow oil. MS (ESI, m/z): 352.6 (M+H+).

Provenance & Evidence