Jozef Hodyl PhD Thesis - Theses - Flinders University

1-(2-hydroxypropyl)-4,7,10-tris-((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane, 5151To a pressure vessel containing a solution of 46 (600 mg, 0.963 mmol) in dryCH 3 CN (1 cm 3 ) and LiBr (262 mg, 0.302 mmol), (S)-(-)-propylene oxide, 75, (0.088g, 1.51 mmol) was added. The mixture was stirred at 80 o C for 3 days. The reactionwas then diluted with 20 cm 3 of de-ionised water and extracted with CHCl 3 (3 x 10cm 3 ). The extracts were dried over MgSO 4 and then concentrated in vacuo to yield,51, as a brown oil, 630 mg, 96%. 1 H NMR (CDCl 3 ): δ 7.3 (6 H, m, ArH); 6.9 (9 H,m, ArH); 4.8 - 2.8 (37 H br m, -CH 2 , -OH & -CH); 1.3 (3 H, br s, (-CH 3 ). 13 C NMR(CD 3 Cl 3 ): δ 158.35 (2 C, Ar, ipso); 158.32 (1 C, Ar, ipso); 129.25 (6 C, Ar); 120.92(2 C, Ar); 120.73 (1 C, Ar) 114.57 (2 C, Ar); 114.49 (2 C, Ar); 114.39 (2 C, Ar);70.13 (1 C, OCH 2 ); 70.04 (2 C, OCH 2 ); 67.84 (1 C, CH); 65.89 (1 C, CH); 65.67 (1C, CH); 65.34 (1C, CH); 63.26 (1 C, -CH 2 N) 58.04 (1 C, CH 2 N); 56.92 (2 C, CH 2 N);52.33 (2 C, cyclen CH 2 ); 51.04 (2 C, cyclen CH 2 ); 50.36 (2 C, cyclen CH 2 ); 49.71 (2C, cyclen CH 2 ); 21.87 (1 C, -CH 3 ).144