A method for the synthesis of hydroxamic acids on solid phase

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 8045-8048

  Floyd, Christopher D ^a   Lewis, Christopher N ^a   Patel, Sanjay R ^a   Whittaker, Mark ^a  

^a British Biotech Pharmaceuticals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; SULFONAMIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605136     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01821-7     Document Type: Article

References (14)

1. 1. Beckett, R.P.; Davidson, A.H.; Drummond, A.H.; Huxley, P. and Whittaker, M., Drug Discovery Today, (1996), 1, 16-26.
2. 2. Cody, R.D.; De Witt, S.H.H.; Hodges, J.C., Kiely; J.S.; Moos, W.H.; Pavia, M.R.; Roth, B.D.; Schroeder, M.C. and Stankovic, C.J., U.S. Patent (1994), USP 5 324-483.
3. 3. Pirrung, M.C. and Chau, J.H-L., J. Org. Chem., (1995), 60, 8084.
4. 4. Atherton, E. and Sheppard, R.C., Solid Phase Synthesis a practical approach, IRL, Oxford, 1989.
5. 3) and dried. Ir (KBr) showed the absence of any carbonyl containing substituent confirming hydrazinolysis of the phthalimide. Elemental analysis of the resin confirmed the presence of nitrogen and suggested a loading of 0.68 mmol/g: C 89.17, H 7.70, N 0.95%. [The loading obtained varied for different batches of the resin due to variability in the loading of the starting resin, but in each case elemental analysis indicated that quantative conversion was achieved.]
6. 6. a) Johnson, W.H.; Roberts, N.A. and Borkakoti, N., J. Enzyme Inhibition, (1987), 2, 1.
7. b) Odake, S.; Okayama, T.; Obata, M.; Morikawa, T.; Hattori, H.; Hori, H., and Nagai, Y., Chem. Pharm. Bull., (1990), 38, 1007.
8. 7. Knorr, R.; Trzeciak, A.; Bannwarth, W. and Gillessen, D., (1989), Tetrahedron Lett, 15, 1927.
9. 50 values of 8.0 μM, 3.5 μM and 8.0 μM respectively.
10. 9. a) MacPherson, L.J. and Parker, D.T., European Patent Application (1994), EP-606,046-A;
11. b) Miller, A., Whittaker, M. and Beckett, R.P., PCT Patent Applications (1995), WO-9535275 and WO-9535276.
12. 10. Zuckermann, R.N.; Kerr, J.M.; Kent, S.B.H. and Moos, W.H., J. Am. Chem. Soc., (1992), 114, 10647.
13. 11. The efficiency of the conversion was measured by loading the resin with excess bromoacetic acid. Elemental analysis (C, N, Br) established a loading value comparable to that for the starting resin.
14. 12. Floyd, C.D.; Lewis, C.N. and Whittaker, M., Chem, Br., (1996), 32, 31.