反应详情

A mixture of Example 39H (23.8 mg, 0.050 mmol), pyridine (31.6 mg, 0.40 mmol), and 2-naphthalenesulfonyl chloride (45.3 mg, 0.20 mmol) in acetone (1.5 mL) was stirred at rt for 18 h. The reaction mixture was evaporated in vacuo and partitioned between ethyl acetate and 1 N HCl. The organic phase was separated, dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with 4:1 hexane/ethyl acetate to provide the title compound (12.3 mg, 39% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.37 (m, 1H) 0.66 (d, J=6.62 Hz, 3H) 0.68 (d, J=6.62 Hz, 3H) 0.77 (m, 1H) 1.29 (m, 1H) 1.52 (s, 3H) 2.02 (m, 1H) 2.18 (m, 1H) 7.52 (m, 4H) 7.68 (m, 2H) 7.73 (d, J=4.04 Hz, 2H) 7.79 (dd, J=8.46, 1.84 Hz, 1H) 8.01 (d, J=7.72 Hz, 1H) 8.13 (m, 3H) 8.50 (s, 1H) 10.93 (s, 1H) 13.71 (s, 1H). MS (ESI+) m/z 630.0 (M+H)+, 647.1 (M+NH4)+, (ESI−) m/z 628.1 (M−H)−.

1. customThe reaction mixture was evaporated in vacuo
2. custompartitioned between ethyl acetate and 1 N HCl
3. customThe organic phase was separated
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe residue was purified by chromatography on silica gel eluting with 4:1 hexane/ethyl acetate