Triacetoxyperiodinane → HCID 118398909, 화합물
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[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:40])[C:7]=1[CH:8]([OH:39])[CH2:9][N:10]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@@H:24]([CH3:33])[CH2:23]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:40])[C:7]=1[C:8](=[O:39])[CH2:9][N:10]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@@H:24]([CH3:33])[CH2:23]2)[C:17]=1[C:18]([F:20])([F:21])[F:19])=[O:12]참가 물질
4
실험 절차
To a light-yellow clear solution of (1S,2S,4S)-ethyl 4-(4-((2-(3,5-dichloropyridin-4-yl)-2-hydroxyethyl)(neopentyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)-2-methylcyclohexanecarboxylate with its (1R,2R,4R)-isomer (0.4702 g, 0.774 mmol) in DCM (12.90 ml) was added Dess-Martin periodinane (0.492 g, 1.161 mmol). The white cloudy mixture was stirred at room temperature. After 2 h, the mixture was quenched with saturated aqueous NaHCO3 (30 mL) and saturated aqueous Na2S2O3 (30 mL). The reaction mixture was extracted with DCM (2×50 mL). The organic extract was dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a colorless syrup. The crude material was absorbed onto a plug of silica gel and purified by silica gel column chromatography eluting with a gradient of 0% to 50% EtOAc in hexane to give (1S,2S,4S)-ethyl 4-(4-((2-(3,5-dichloropyridin-4-yl)-2-oxoethyl)(neopentyl)carbamoyl)-5-(trifluoro methyl)-1H-pyrazol-1-yl)-2-methylcyclohexanecarboxylate with its (1R,2R,4R)-isomer (0.437 g, 0.722 mmol, 93% yield): 1H NMR (400 MHz, CDCl3) δ 8.46-8.61 (2H, m), 7.51-7.74 (1H, m), 4.49-4.92 (2H, m), 4.25-4.39 (1H, m), 4.18 (2H, q, J=7.1 Hz), 3.29-3.61 (2H, m), 1.63-2.18 (8H, m), 1.29 (3H, t, J=7.1 Hz), 0.81-1.06 (12H, m), rotamers present; LCMS (ESI) m/z 605.0 (M+H)+.