반응 #1098644

반응 방정식

fluoroazide

1-Azido-3-fluoropropan-2-ol

1-propynyl-2-nitroimidazole

THF

sodium ascorbate

→

pale yellow crystals

수율 4.2%

1-Fluoro-3-(4-((2-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propan-2-ol

수율 4.2%

용매

water

t-BuOH

반응 조건

후처리

1. 1
   workup.ADDITIONthe reaction was poured onto EtOAc
2. 2
   세척washed with NH4OH
3. 3
   기타the material was then purified on a silica gel column
4. 4
   기타The material was then further purified via recrystallization

실험 절차

To a vial was added fluoroazide 17 (690 mg, 5.79 mmol) and 1-propynyl-2-nitroimidazole (876 mg, 5.79 mmol). To this flask was added THF (3 mL), t-BuOH (3 mL), water (3 mL), CuSO4 (185 mg, 1.16 mmol) and sodium ascorbate (1.15 g, 5.79 mmol). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the material was then purified on a silica gel column using EtOAc:Hex as the eluent. The material was then further purified via recrystallization using EtOAc:Hex to afford 65 mg (4% yield) of pale yellow crystals. 1H NMR (DMSO-d6, 400 MHz), δ: 4.04 (1H, br d, J=20.4 Hz), 4.20-4.47 (4H, m), 5.53 (1H, br s), 5.66 (2H, s), 7.16, (1H, s), 7.68 (1H, s), 8.05 (1H), s).

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