Trichloroacetic Acid → HCID 86680158, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,2,2-trifluoro-N-[(4R)-5-(methoxymethylene)-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]acetamide (1060 mg, 2.81 mmol) in chloroform (90 mL) was added trichloroacetic acid (1.84 g, 11.24 mmol). The mixture was heated at 70° C. overnight and another portion of trichloroacetic acid (1.84 g, 11.24 mmol) was added and heating continued for 6 h. After cooling to room temperature, the reaction was quenched with saturated sodium bicarbonate and extracted with DCM 3×. The combined organic layers were concentrated and the residue was purified via silica gel column chromatography (0-100% EA/heptane) to give 2,2,2-trifluoro-N-[(4R)-5-formyl-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]acetamide (896 mg, 88%).

Provenance & Evidence