Nitrogen → 5-Phenyl-oxazole-4-carboxylic acid {1-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-1H-pyrazol-3-yl}-amide

Participants

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 5-phenyl-oxazole-4-carboxylic acid (1-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-yl)-amide (271 mg, 0.55 mmol) in dry THF (5.5 mL) was treated at 0° C. with TBAF (1.1 mL of a 1M solution in THF, 1.1 mmol). The reaction mixture was stirred at 0° C. for 30 min. The mixture was then diluted with EA (10 mL), washed with NaHCO3 (10 mL) followed by brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (EA) gave the title compound as a white foam. TLC: rf (EA)=0.18. LC-MS-conditions 02: tR=0.87 min; [M+H]+=380.34.

Provenance & Evidence