Triacetoxyperiodinane → HCID 23648431, compound

Participants

Reaction Steps

To a solution of 90 mg (0.14 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 2 mL of dichloromethane was added 76 mg (0.18 mmol) of Dess-Martin periodinane. The reaction mixture was stirred for 15 min, and then filtered through a celite plug with dichloromethane. The filtrate was concentrated, and the residue was purified by silica gel chromatography eluting with ethyl acetate:hexanes (6.5:3.5) to afford 56 mg (62%) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate. 1H-NMR (300 MHz, T=100° C., DMSO6): δ 8.66 (d, J=4 Hz, 1H), 8.08–7.60 (m, 9H), 7.17 (m, 1H), 6.72 (d, J=2 Hz, 1H), 4.90 (d, J=9 Hz, 1H), 4.49 (d, J=14 Hz, 1H), 4.26–3.85 (m, 4H), 1.56 (m, 1H), 1.40 (m, 1H), 1.29–1.01 (m, 13H) 0.78 (m, 3H); ES-LCMS m/z 646 (M+Na); HRMS C29H36F3N5O5S1 m/z 646.2287 (M+Na)+Cal; 646.2283 (M+Na)+.

Provenance & Evidence