Jozef Hodyl PhD Thesis - Theses - Flinders University

1,4,7-tris-((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane•4HCl, 91HHOOOHHONHNH 2HNHNHOHO4Cl91A solution of 46 (400 mg, 0.64 mmol), in ice-cold dry EtOH (5 cm 3 ) was treateddropwise with 37% HCl, (10 cm 3 , 121.00 mmol), over 10 min. and then stirred for afurther 2 h. The resultant mixture was then concentrated in vacuo and redissolved inMeOH (0.5 cm 3 ), precipitated and then triturated with of Et 2 O to give an off-whitesolid, which was filtered, washed with Et 2 O (10 cm 3 ) and dried under reducedpressure, to yield 91 426 mg, 86%. 13 C NMR (CD 3 OD): δ 159.95 (2 C, Ar, ipso);159.73 (1 C, Ar, ipso); 130.56 (6 C, Ar); 122.33 (2 C, Ar); 122.11 (1 C, Ar); 115.68(6 C, Ar); 71.20 (2 C, OCH 2 ); 70.85 (1 C, OCH 2 ); 67.44 (1 C, CH); 65.67 (2 C, CH);58.37 (1 C, CH 2 N); 57.80 (2C, CH 2 N); 52.20 (2 C, cyclen -CH 2 ); 51.89 (2 C, cyclen-CH 2 ); 44.20 (2 C, cyclen -CH 2 ); 43.74 (2 C, cyclen -CH 2 ). (Found C, 54.54; H,6.88; N, 7.57 C 35 H 54 Cl 4 N 4 O 6 requires C, 54.69; H, 7.08; N, 7.29%).139