反应详情

To a solution of 3-amino-biphenyl (315, 536 mg, 3.17 mmol) in THF/pyridine (2:1, 6 mL) was added methyl 7-(chlorocarbonyl)heptanoate (0.49 mL, 3.48 mmol), and the resulting solution was stirred at room temperature for 16 h. After dilution with saturated NaCl solution (15 mL) and extraction with ethyl acetate, the organic layer was dried over Na2SO4, filtered and concentrated. The residue was then dissolved in THF/methanol/H2O (1:1:2, 8 mL), followed by the treatment of LiOH—H2O (665 mg, 15.85 mmol). The reaction mixture was stirred at room temperature for 1 h prior to acidification (pH=1), and extraction with ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated. After purification by flash chromatography (eluent 0-100% EtOAc in hexanes), the title compound 316 was obtained as a white solid (889 mg, 86% yield). 1H NMR: (DMSO) δ (ppm): 1.30-1.40 (m, 4H), 1.50-1.59 (m, 2H), 1.60-1.68 (m, 2H), 2.24 (t, J=7.4 Hz, 2H), 2.37 (t, J=7.4 Hz, 2H), 7.32 (dt, J=7.8, 1.6 Hz, 1H), 7.36-7.42 (m, 2H), 7.46-7.52 (m, 2H), 7.58-7.64 (m, 3H), 7.96 (s, 1H), 10.07 (br s, 1H). MS: (calc.) 325.4; (obt.) 326.1 (MH)+.

1. extractionAfter dilution with saturated NaCl solution (15 mL) and extraction with ethyl acetate
2. dry with materialthe organic layer was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe residue was then dissolved in THF/methanol/H2O (1:1:2, 8 mL)
6. stirringThe reaction mixture was stirred at room temperature for 1 h
7. extractionto acidification (pH=1), and extraction with ethyl acetate
8. dry with materialThe organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customAfter purification by flash chromatography (eluent 0-100% EtOAc in hexanes)