Jozef Hodyl PhD Thesis - Theses - Flinders University

1-(benzyloxycarbonyl)-4,7,10-tris-((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane•3HCl, 90OHOOONH 2NNHHNHO3Cl -OOHO90To a solution of 71 (796 mg, 1.05 mmol), dissolved in dry EtOH (5 cm 3 ) andstirred at 0 o C was added 36% HCl, (10 cm 3 , 116.50 mmol). The mixture was stirredfor 2 h, after which the solvent was removed in vacuo. The white solid obtained wasredissolved in EtOH and precipitated with Et 2 O filtered, and washed with ice-coldEtOH (5 cm 3 ) and Et 2 O (5 cm 3 ) to yield 90 as a white solid, 840 mg, 92%. 13 C NMR(CD 3 OD): δ 159.90 (1 C, C=O); 159.63 (3 C, Ph, ipso); 136.7 (1 C, Bn, ipso); 130.57(6 C, Ph); 129.91 (1 C, Bn); 129.70 (4 C, Bn); 122.30 (2 C, Ph); 122.17 (1 C, Ph);115.70 (6 C, Ph); 70.98 (3 C, OCH 2 ); 70.01 (1 C, -CH 2 Bn); 67.90 (1 C, CH); 65.95(2 C, CH); 58.1 (1 C, CH 2 N); 57.80 (2 C, CH 2 N); 53.69 (2 C, cyclen -CH 2 ); 52.10 (2C, cyclen -CH 2 ); 50.80 (2 C, cyclen -CH 2 ); 46.01 (2 C, cyclen -CH 2 ). (Found C,59.52; H, 6.98; N, 6.30. C 43 H 60 Cl 3 N 4 O 8 requires C, 59.55; H, 6.97; N, 6.46%).137