反应详情

Trifluoroacetic acid (3.0 mL, 39 mmol) was added to a solution of the product of Example 166C (279 mg, 0.439 mmol) in CH2Cl2 (3 mL), and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction was then cooled to 0° C., diluted with CH2Cl2 (25 mL) and quenched by slow addition of 2 N aqueous NaOH solution (25 mL). The mixture was separated and the aqueous phase was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Ether was added to the residue which caused a solid to form, which was collected by vacuum filtration and washed with minimal ether and air-dried. The material was then chromatographed on silica gel (Analogix® Intelliflash™ 280; SF10-8 g column; 10% methanol/CH2Cl2) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.68 (d, J=8.3, 2H), 7.36 (d, J=8.2, 2H), 7.32-7.15 (m, 10H), 4.85-4.69 (m, 1H), 3.68 (s, 2H), 3.45 (t, J=6.4, 2H), 3.17-3.06 (m, 2H), 2.76 (td, J=12.4, 1.9, 2H), 2.66-2.56 (m, 2H), 2.00-1.65 (m, 5H), 1.40-1.21 (m, 2H); MS (DCI+) m/z 536 (M+H)+.

1. temperatureThe reaction was then cooled to 0° C.
2. customquenched by slow addition of 2 N aqueous NaOH solution (25 mL)
3. customThe mixture was separated
4. extractionthe aqueous phase was extracted with CH2Cl2
5. washThe combined organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. additionEther was added to the residue which
10. customto form
11. filtrationwhich was collected by vacuum filtration
12. washwashed with minimal ether
13. customair-dried
14. customThe material was then chromatographed on silica gel (Analogix® Intelliflash™ 280; SF10-8 g column; 10% methanol/CH2Cl2)