Triacetoxyperiodinane → HCID 23648430, compound

Participants

Reaction Steps

To a solution of 0.130 g (0.22 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate in 2.0 mL of dichloromethane was added 0.020 g (0.24 mmol) of sodium bicarbonate and 0.11 g (0.26 mmol) of Dess-Martin periodinane. The reaction mixture was stirred for 15 min and then purified via silica gel chromatography eluting with ethyl acetate:hexane (7:3) to afford 0.078 g (59%) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl(1S)-1-methyl-2-oxo-3-[(2-pyridinylsulfonyl)amino]propylcarbamate as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 8.58 (m, 1H), 7.98–7.89 (m, 4H), 7.63 (m, 2H), 7.46 (m, 2H), 6.65 (s, 1H), 5.56 (m, 1H), 1.05 (s, 9H), 5.24 (d, J=7 Hz, 1H), 4.98 (m, 1H), 4.44 (m, 1H), 4.34–4.12 (m, 4H), 1.12 (d, J=7 Hz, 3H); LC-MS m/z 582 (M+H).

Provenance & Evidence