On the synthesis of 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10- tetraazacyclododecane

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2058-2061

  Jagadish, Bhumasamudram ^a   Brickert Albrecht, Gayle L ^a   Nichol, Gary S ^a   Mash, Eugene A ^a   Raghunand, Natarajan ^b  

^a University of Arizona   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

Author keywords

Contrast agent; DO3A; DOTA; MRI; Synthesis; X ray crystallography

Indexed keywords

1,4,7 TRI[TERT BUTOXYCARBONYLMETHYL] 1,4,7,10 TETRAAZACYCLODODECANE; BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 79953182650     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.074     Document Type: Article

References (30)

1. Lauffer, R. B. Chem. Rev. 1987, 87, 901-927.
2. Tóth, É.; Helm, L.; Merbach, A. E. Top. Curr. Chem. 2002, 221, 61-101.
3. Westbrook, C.; Roth, C. K.; Talbot, J. MRI in Practice, 3rd ed.; Blackwell: Malden, MA, 2005.
4. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293-2352.
5. Caravan, P. Chem. Soc. Rev. 2006, 35, 512-523.
6. Hermann, P.; Kotek, J.; Kubìcek, V.; Lukes, I. Dalton Trans. 2008, 3027-3047.
7. Bonnet, C. S.; Tóth, É. Am. J. Neuroradiol. 2010, 31, 401-409.
8. Barge, A.; Tei, L.; Upadhyaya, D.; Fedeli, F.; Beltrami, L.; Stefanìa, R.; Aime, S.; Cravotto, G. Org. Biomol. Chem. 2008, 6, 1176-1184.
9. Himmelsbach, R. J.; Rongved, P.; Klaveness, J.; Strande, P.; Dugstad, H. WO 93/02045.
10. Berg, A.; Almen, T.; Klaveness, J.; Rongved, P.; Thomassen, T. U.S. 5198,208.
11. Axelsson, O.; Olsson, A. WO 2006/112723 A1.
12. Moore, D. A. Org. Synth. 2008, 85, 10-14.
13. Dadabhoy, A.; Faulkner, S.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 2 2002, 348-357.
14. Prasuhn, D. E.; Yeh, R. M.; Obenaus, A.; Manchester, M.; Finn, M. G. Chem. Commun. 2007, 1269-1271.
15. Mizukami, S.; Tonai, K.; Kaneko, M.; Kikuchi, K. J. Am. Chem. Soc. 2008, 130, 14376-14377.
16. Li, C.; Wong, W.-T. Tetrahedron 2004, 60, 5595-5601.
17. Kohl, S. W.; Kuse, K.; Hummert, M.; Schumann, H.; Mügge, C.; Janek, K.; Weißhoff, H. Z. Naturforsch. 2007, 62b, 397-406.
18. Moore, D. A. WO 2007/106546 A2.
19. Liu, W.; Hajibeigi, A.; Lin, M.; Rostollan, C. L.; Kovacs, Z.; Öz, O. K.; Sun, X. Bioorg. Med. Chem. Lett. 2008, 18, 4789-4793.
20. Ke, T.; Feng, Y.; Guo, J.; Parker, D. L.; Lu, Z.-R. Magn. Reson. Imaging 2006, 24, 931-940.
21. Rami, M.; Cecchi, A.; Montero, J.-L.; Innocenti, A.; Vullo, D.; Scozzafava, A.; Winum, J.-Y.; Supuran, C. T. ChemMedChem 2008, 3, 1780-1788.
22. Machitani, K.; Sakamoto, H.; Nakahara, Y.; Kimura, K. Anal. Sci. 2008, 24, 463-469.
23. Chong, H.-S.; Lim, S.; Baidoo, K. E.; Milenic, D. E.; Ma, X.; Jia, F.; Song, H. A.; Brechbiel, M. W.; Lewis, M. R. Bioorg. Med. Chem. Lett. 2008, 18, 5792-5795.
24. Yoo, B.; Sheth, V. R.; Pagel, M. D. Tetrahedron Lett. 2009, 50, 4459-4462.
25. Raghunand, N.; Guntle, G. P.; Gokhale, V.; Nichol, G. S.; Mash, E. A.; Jagadish, B. J. Med. Chem. 2010, 53, 6747-6757.
26. 2 >2σ), wR2 = 0.0768 (all data).
27. 2 >2σ), wR2 = 0.1559 (all data).
28. 2 >2σ), wR2 = 0.0971 (all data).
29. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-795054, CCDC-793547, and CCDC-793548 for compounds 3, 4, and 5, respectively. Copies of the data can be obtained, free of charge, on application to CCDC by e-mail: deposit@ccdc.cam. ac.uk.
30. Mills, J. E.; Maryanoff, C. A.; McComsey, D. F.; Stanzione, R. C.; Scott, L. J. Org. Chem. 1987, 52, 1857-1859.