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

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+).

1. customthe resulting reaction mixture
2. stirringwas stirred at room temperature for 2 hours
3. stirringThe reaction was then stirred at 130° C. under microwave radiation for 30 minutes
4. concentrationThe reaction mixture was concentrated in vacuo
5. dissolutionThe residue was dissolved in ethylacetate
6. extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
7. dry with materialThe organic phase was dried over sodium sulfate
8. customevaporated down to dryness
9. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient

ORD record

ord-44e55c1293f945a3bfafa5c0042331fa

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409866B2