反应详情

温度

25 °C

A solution containing the product from Example 3G (6.18 g, 26.9 mmol) in dichloromethane (160 mL) was treated with 6-methyl-2-pyridinecarboxaldehyde (3.25 g, 26.8 mmol) and magnesium sulfate (16.3 g, 135.4 mmol) g), stirred at 25° C. for 18 hours, filtered and concentrated. A solution of the residue in methanol (160 mL) was treated with sodium borohydride (1.2 g, 31.7 mmol), stirred at 25° C. for 1 hour, quenched with water, stirred for 15 minutes, and followed by evaporation of the solvent. The concentrate was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the residue (9.1 g, 26.8 mmol) in 1,2-dichloroethane (550 mL) was treated with N,N-disuccinimidyl carbonate (8.24 g, 32.2 mmol) and triethylamine (3.7 mL, 26.5 mmol), stirred at 25° C. for 68 hours, partitioned with 10% Na2CO3, and the organic phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloroform to give the title compound (6.15 g, 63% yield).

1. filtrationfiltered
2. concentrationconcentrated
3. stirringstirred at 25° C. for 1 hour
4. customquenched with water
5. stirringstirred for 15 minutes
6. customfollowed by evaporation of the solvent
7. customThe concentrate was partitioned between ethyl acetate and saturated NaHCO3
8. washthe organic phase was washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. stirringstirred at 25° C. for 68 hours
13. custompartitioned with 10% Na2CO3
14. washthe organic phase was washed with additional 10% Na2CO3 solution and brine
15. dry with materialdried over MgSO4
16. filtrationfiltered
17. concentrationconcentrated
18. customThe residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloroform