反应详情

温度

80 °C

A 0.66 M solution of L-ascorbic acid is prepared by dissolving L-ascorbic acid sodium salt (0.79 g, 2.0 mmol) in water (6 mL). N-((4aS,7aS)-7a-(3-bromophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (1.40 g, 3.35 mmol) and 1,2-cyclohexanediamine, N,N′-dimethyl-, trans (+/−) (162 mg, 1.11 mmol) are dissolved in ethanol (13.4 mL). Sodium azide (0.661 g, 10.1 mmol) is added. The 0.66 M aqueous L-ascorbic acid sodium salt (2.24 mL) and water (2.58 mL) are added. The reaction flask is fitted with a reflux condenser and the mixture is degassed and evacuated with nitrogen. Copper (II) sulfate pentahydrate (0.184 g, 0.738 mmol) is added and the reaction flask is heated to 80° C. and stirred for 1.5 h. The reaction mixture is cooled to room temperature and ice water is added. The reaction mixture is extracted three times with ethyl acetate. The combined organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure to give a residue that is purified on silica gel with 50% ethyl acetate in hexanes to give the title compound (0.620 g, 49%). Further elution of the flash column with 100% ethyl acetate yields more title compound (0.488 g, 41%). ES/MS m/e: 380 (M+1).

1. customThe reaction flask is fitted with a reflux condenser
2. customthe mixture is degassed
3. customevacuated with nitrogen
4. temperatureThe reaction mixture is cooled to room temperature
5. extractionThe reaction mixture is extracted three times with ethyl acetate
6. dry with materialThe combined organic phase is dried over sodium sulfate
7. customthe solvent is removed under reduced pressure
8. customto give a residue that
9. customis purified on silica gel with 50% ethyl acetate in hexanes