1: 0.235 g
2: 0.126 g |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; |
1
To a flask containing N,N'-(5,5'-(thiobis(ethane-2,l-diyl))bis(l,3,4-thiadiazole-5,2- diyl))bis(2-phenylacetamide) (1) (9.4 mmol, 5.0 g, 1.0 equiv.) was added 100 mL DMF, K2C03 (20.98 mmol, 2.89 g, 2.2 equiv.), and chloromethyl butyrate (20.98 mmol, 2.86 g, 2.62 mL, 2.2 equiv.). The mixture stirred at room temperature for 15 hours then diluted with 200 mL water and 200 mL EtOAc. The layers were separated and the aqueous layer extracted with EtOAc (2 x 100 mL) and the organic layers combined, washed with water, brine and dried over Na2S04. The Na2S04 was removed by filtration and the volatiles removed under reduced pressure. The compounds were purified by reverse phase chromatography (MeCN, H20) giving 0.235 g of compound 8 and 0.126 g of compound 7. 1HNMR (300 MHz, DMSO, d6) Compound 8: δ 7.31 (m, 10H), 6.18 (s, 4H), 3.82 (s, 4H), 3.17 (dd, 2H, J=6.8 Hz), 2.92 (dd, 2H, J=6.8 Hz), 2.93 (m, 4H), 2.32 (dd, 2H, J=7.2 Hz), 1.54 (dt, 2H, J =7.2, 7.4 Hz), 0.87 (t, 3H, J= 7.4Hz). 1HNMR (300 MHz, DMSO, d6) Compound 7: δ 12.68 (s, 1H), 7.32 (m, 10H), 6.18 (s, 2H), 3.82 (s, 4H), 3.26 (dd, 2H, J=7.0 Hz), 3.17 (dd, 2H, J=6.8 Hz), 2.93 (m, 4H), 2.32 (dd, 2H, J =7.2 Hz), 1.54 (dt, 2H, J =7.2, 7.4 Hz), 0.87 (t, 3H, J = 7.4Hz). |