反应详情

温度

80 °C

A 0.33 M solution of copper sulfate is prepared by dissolving copper (II) sulfate pentahydrate (1.0 g, 2.0 mmol) in water (12 mL). A 0.66 M solution of L-ascorbic acid is prepared by dissolving L-ascorbic acid sodium salt (1.58 g, 4.0 mmol) in water (12 mL). To a solution of tert-butyl (8aS)-8a-(3-bromophenyl)-4,4a,5,7,8,8a-hexahydropyrano[4,3-d][1,3]thiazin-2-ylcarbamate (0.500 g, 1.20 mmol) in ethanol (3.6 mL) is added sodium azide (0.228 g, 3.50 mmol), 1,2-cyclohexanediamine, N,N′-dimethyl-, trans (+/−) (0.0549 g, 0.386 mmol), 0.66 M aqueous L-ascorbic acid sodium salt (0.772 mL, 0.509 mmol), and water (0.71 mL) and the mixture is purged with nitrogen. A 0.33 M aqueous solution of copper (II) sulfate pentahydrate (0.773 mL, 0.255 mmol) is added and the reaction is heated to 80° C. for 12 min. The reaction is poured into cold water to afford a blue mixture that is extracted three times with EtOAc. The organic layer is dried over Na2SO4 to afford crude material which is purified by silica gel chromatography eluting with a linear gradient of 5% to 100% EtOAc in hexanes to give the title compound (0.400 g, 88%). ES/MS m/e: 390 (M+1).

1. customthe mixture is purged with nitrogen
2. customto afford a blue mixture that
3. extractionis extracted three times with EtOAc
4. dry with materialThe organic layer is dried over Na2SO4
5. customto afford crude material which
6. customis purified by silica gel chromatography
7. washeluting with a linear gradient of 5% to 100% EtOAc in hexanes