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With sodium hydrogencarbonate; In water; acetone; at 20.0℃; for 4h; |
Example 9; Synthesis of Compound 16 of Example 1; Acid 12 (46 mg, 0.12 mmol) was dissolved in MeOH (4 mL) and hydrogenated for 20 min. using 20% wt Pd/C. The solution was filtered and the solvent was evaporated in vacuo. The solid residue was dissolved in aqueous acetone (3 mL, 1:1) and treated with <strong>[<strong>[88744-04-1]8</strong><strong>[88744-04-1]8</strong>744-04-1]9-fluorenylmethyl pentafluorophenyl carbonate</strong> (91 mg, 0.24 mmol) and sodium bicarbonate (31 mg, 0.37 mmol) for 4 hours at room temperature. Water (10 mL) was added and the aqueous layer was extracted with ethyl acetate (6×10 mL). Finally, the solvent was dried (Na2SO4) and concentrated. The crude product was purified by flash column chromatography (methanol:ethyl acteate, 1:1) to afford compound 16 (45 mg, 63%).1H NMR (300 MHz, CD3OD, r.t., TMS): delta=1.43 (s, 9H), 2.9<strong>[88744-04-1]8</strong>-3.13 (m, 2H, H-6+H-<strong>[88744-04-1]8</strong>a), 3.1<strong>[88744-04-1]8</strong> (m, 1H, H-7), 3.22-3.44 (m, 2H, H-3, H-5), 3.62-3.<strong>[88744-04-1]8</strong>0 (m, 2H, H-4, H-<strong>[88744-04-1]8</strong>b), 4.23 (t, 1H, J=6.<strong>[88744-04-1]8</strong> Hz), 4.32-4.4<strong>[88744-04-1]8</strong> (m, 3H), 7.2<strong>[88744-04-1]8</strong>-7.<strong>[88744-04-1]8</strong>7 (m, <strong>[88744-04-1]8</strong>H). 13C NMR (100 MHz, CDCl3, r.t.): delta=2<strong>[88744-04-1]8</strong>.<strong>[88744-04-1]8</strong><strong>[88744-04-1]8</strong>, 43.42, 4<strong>[88744-04-1]8</strong>.54, 56.37, 67.7<strong>[88744-04-1]8</strong>, 72.04, 73.14, 79.03, <strong>[88744-04-1]8</strong>0.3<strong>[88744-04-1]8</strong>, <strong>[88744-04-1]8</strong>0.76, <strong>[88744-04-1]8</strong>2.97, 120.94-12<strong>[88744-04-1]8</strong>.7<strong>[88744-04-1]8</strong> (aromatic carbons), 142.61-145.43 (aromatic carbons), 157.71, 159.12, 169.46. MS (ES, [M-H]-); Anal. Calcd for C2<strong>[88744-04-1]8</strong>H33N2O10: 557.21, Found: 557.09. HRMS (ES, [M-H]-); Anal. Calcd for C2<strong>[88744-04-1]8</strong>H33N2O10: 557.2135, Found: 5<strong>[88744-04-1]8</strong>1.2133. |