Nitrogen → 2-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-4-nitro-2H-[1,2,3]triazole

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Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazole (247 mg, 0.89 mmol) in DMF (1.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (850 mg of a 10% solution in acetone, 0.75 mmol) in DMF (1.0 mL) pre-treated for 30 min with DIPEA (0.26 mL, 1.49 mmol) and the reaction mixture was stirred for 48 h at 50° C. Water (10 mL), followed by EA (20 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a yellow oil. TLC:rf (2:1 hept-EA)=0.36. LC-MS-conditions 02: tR=1.11 min; [M+H]+=354.34.

Provenance & Evidence