Reaction Steps
The mixture of 10 (28 mg), EtOH (0.5 mL), water (0.5 mL), KOH (10 mg) was reflux for 5 h. After cooling, the reaction mixture was acidified with 1M HCl (pH˜6). Then the mixture was extracted with DCM (10 mL×3). The combined organic layer was dried over sodium sulfate. After evaporation of the solvent, 21 mg of yellow solids (74%) was obtained. HPLC/MS: tR=12.10 min; m/z=440.4 [M+H]+ HRMS: C24H27N3O3Cl, 440.1741 (calcd.), 440.1721 (found). 1H NMR (600 MHz, DMSO, a mixture of rotamers): 0.85-1.63 (m, 16H), 3.57 (m, 2H), 4.17 (ABd, 1H, J=16.2 Hz), 4.22 (ABd, 1H, J=15.6 Hz), 4.67 (ABd, 1H, J=16.8 Hz), 4.88 (ABd, 1H, J=15.6 Hz), 6.10 (s, 1H), 6.51 (m, 1H), 6.60 (s, 1H), 6.78 (m, 2H), 6.91-7.28 (m, 7H), 7.66-7.91 (m, 4H), 8.27 (s, 1H), 8.34 (s, 1H), 11.56 (s, 1H), 11.88 (s, 1H), 13.15 (br.s, 1H), 13.53 (br.s, 1H). 13C NMR (150 MHz, DMSO, a mixture of rotamers): 25.0, 25.1, 25.5, 32.5, 32.6, 47.0, 48.5, 56.2, 112.4, 121.3, 122.4, 125.2, 125.8, 126.7, 126.8, 127.1, 127.7, 127.9, 129.0, 129.3, 136.4, 138.0, 164.2, 168.8.
