Tetrabutylammonium Fluoride → HCID 15344101, compound

Participants

Reaction Steps

A solution of 74.5 mg (0.117 mmol) of (2S,3S,5S)-2-(Boc-amino)-5-(N-((3-pyridinyl)methoxycarbonyl)amino)-1-phenyl-6-(4-pyridinyl)-3-(tert-butyldimethylsilyloxy)-hexane in 4 ml of tetrahydrofuran was treated with 102 μl of 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. After being stirred at ambient temperature for 24 h, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography using 10% methanol in dichloromethane to provide 51.4 mg (84%) of the desired compound as a white solid. 1H NMR (CDCl3) δ1.37 (s, 9H), 1.65 (t, 2H), 2.82-3.01 (m, 5H), 3.70 (m, 2H), 4.03 (m, 1H), 4.78 (d, 1H), 5.03 (s, 2H), 5.18 (br d, 1H), 7.06 (d, 2H), 7.16-7.31 (m, 6H), 7.61 (d, 1H), 8.44 (d, 2H), 8.57 (s, 2H). Mass spectrum: (M+H)+ =521.

Provenance & Evidence