反应详情

Diethyl 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonate (Cpd. No. 1, 50 mg, 0.09 mmol) was dissolved in anhydrous methylene chloride (1 mL). Bromotrimethylsilane (750 μL, 5.7 mmol) was added and the mixture was stirred for 4 h whereupon the LC-MS confirmed the starting material was consumed. The solvent was removed under reduced pressure. The resulting residue was dissolved in methanol:water (1:1, 3 mL) and shaken for 30 min. The mixture was filtered over a pad of Celite. The Celite was washed with ethyl acetate. The combined filtrates were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonic acid (Cpd. No. 2) as a white solid. 1H NMR (DMSO-d6): 8.02 (m, 2H), 7.69-7.56 (m, 5H), 7.38 (s, 1H), 6.33 (s, 1H), 3.86 (m, 2H), 1.83 ppm (m, 1H). MW=524 confirmed by LC-MS, tr=11.24 min (Method Y) MH+=522-526.

1. customwas consumed
2. customThe solvent was removed under reduced pressure
3. dissolutionThe resulting residue was dissolved in methanol:water (1:1, 3 mL)
4. stirringshaken for 30 min
5. filtrationThe mixture was filtered over a pad of Celite
6. washThe Celite was washed with ethyl acetate
7. washThe combined filtrates were washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure