反应详情

To a solution of tert-butyl [2-[(4-{1 [(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoyl)amino]-4-(3-thienyl)phenyl]carbamate (164 mg, 0.27 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (2 mL), and the reaction was stirred at room temperature for 2 h. Concentration yielded a yellow residue that was dissolved in EtOAc, neutralized with sat. NaHCO3, washed with brine, dried (MgSO4), and evaporated. The resulting solid was dissolved in CH2Cl2 (15 mL) and MeOH (0.5 mL). Hexanes (5 mL) were added, and upon concentration to half-volume, the mixture was filtered to isolate 4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}-N-[2-amino-5-(3-thienyl)phenyl]benzamide as a white solid. 1H NMR (DMSO-d6) δ10.19 (s, 1H), 9.66 (s, 1H), 8.12 (t, J=5.7 Hz, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.58 (d, J=7.6 Hz, 2H), 7.54-7.52 (m, 2H), 7.49-7.47 (m, 3H), 7.38 (dd, J=4.7, 1.5 Hz, 1H), 7.33 (dd, J=8.2, 2.1 Hz, 1H), 7.26 (t, J=7.9 Hz, 2H), 7.01 (t, J=7.5 Hz, 1H), 6.78 (d, J=8.5 Hz, 1H), 4.99 (s, 2H), 4.06 (dd, J=8.5, 6.2 Hz, 1H), 3.54 (ddd, J=13.3, 8.5, 5.0 Hz, 1H), 3.47 (dt, J=12.9, 6.2 Hz, 1H), 1.76 (s, 3H). MS (ESI) calcd [M+H]+ 499.1, found 499.1.

1. concentrationConcentration
2. customyielded a yellow residue that
3. washwashed with brine
4. dry with materialdried (MgSO4)
5. customevaporated
6. dissolutionThe resulting solid was dissolved in CH2Cl2 (15 mL)
7. additionHexanes (5 mL) were added
8. concentrationupon concentration to half-volume
9. filtrationthe mixture was filtered