Trifluoroacetic acid → Trifluoroacetate

Participants

Reaction Steps

The residue prepared in STEP B above (850 mg, 2.65 mmol) in DMF (10 mL) was combined with 2-bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one (1.04 g, 3.18 mmol) and stirred at room temperature for 18 h. The resulting mixture was evaporated in vacuo to yield an oil, which was treated with 50% TFA in DCM at 0° C. The solvent was then evaporated, and the residue purified via reverse phase HPLC to yield 2-(8-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)-7-imino-2,3,4,7,8,9-hexahydro-[1,4]dioxepino[2,3-f]isoindol-3-yl)acetaldehyde as its corresponding trifluoroacetate salt, as a residue. MS MH+=493; 1H NMR (CDCl3): d 8.88 (bs, 1H), 7.83 (s, 2H), 7.66 (s, 1H), 7.05 (s, 1H), 5.85 (bs, 1H), 4.67 (s, 2H), 4.36 (m, 2H), 4.11 (m, 4H), 2.91 (m, 1H), 2.76 (m, 2H), 1.45 (s, 18H).

Provenance & Evidence