Acetic Acid → [2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl ester

Participants

Reaction Steps

To a solution of acetic acid (139 mg, 132 μl, 2.31 mmol) in dry DMF (8 ml) under an argon atmosphere was added carbonyldiimidazole (374 mg, 2.31 mmol) and the reaction mixture was stirred at room temperature for 45 minutes. Addition of a solution of [2-Cyclopropyl-1-(N-hydroxycarbamimidoyl)-1-methyl-ethyl]-carbamic acid benzyl ester (Example 66c, 0.64 g, 2.2 mmol) in dry DMF (4 ml) and the resulting reaction mixture was stirred at room temperature for 2 hours. The reaction was then stirred at 130° C. under microwave radiation for 30 minutes. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and extracted with an 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 (542 mg, 78%) as a yellow oil. MS (ESI, m/z): 316.5 (M+H+).

Provenance & Evidence