Tetrabutylammonium Fluoride → HCID 135870903, compound

Participants

Reaction Steps

4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-(tert-butyldimethylsilyloxy)-3-chloro-phenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (377 mg, 0.58 mmol) was deprotected using tetrabutylammonium fluoride (1.0 M solution in THF, 1.2 mL, 1.2 mmol) in a manner analogous used for the preparation of Example 22. After column chromatography (80% EtOAc/hexanes) the title compound was isolated as an off-white solid (23 mg). 1H NMR (400 MHz, CDCl3, δ in ppm) 7.91 (d, J=2.2 Hz, 1H), 7.77 (dd, J=2.2, 8.4 Hz, 1H), 7.46 (d, J=8.6 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 5.68 (d, J=8.4 Hz, 1H), 5.08 (dd, J=3.7, 8.4 Hz, 1H), 4.62 (m, 1H), 2.39 (s, 3H), 1.40 (d, J=6.3 Hz, 3H).

Provenance & Evidence