Magic angle spinning NMR: A valuable tool for monitoring the progress of reactions in solid phase synthesis

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4771-4774

  Wehler, Thomas ^a   Westman, Jacob ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PROTEIN SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030200010     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00931-8     Document Type: Article

References (17)

1. 1. a, Gallop M. A., Barrett R. W., Dower W. J., Fodor S. P. A., Gordon E. M. J. Med. Chem. 1994, 37, 1233-1251.
2. b, Gordon E. M., Barrett R. W., Dower W. J., Fodor S. P. A., Gallop M. A. J. Med. Chem. 1994, 37, 1385-1401.
3. 2. a, Barany G., Merrifield R. B. The Peptides; Gross E., Meienhofer J.; Academic Press, Inc.: London, 1979; pp. 3-254.
4. b, Brown T., Brown D. J. S. Oligonucleotides and analogues, Eckstien F: Oxford University Press, New York, 1991; pp. 1-23.
5. 3. Kaiser E., Colescott R. L., Bossinger C. D., Cook P. I. Anal. Biochem. 1970, 34, 595-598.
6. 4. Anderson R. C., Stokes J. P., Shapiro M. J. Tetrahedron Lett. 1995, 36, 5311-5314.
7. 5. a, Sucholeiki I. Med. Chem. Res 1995, 5, 618-630.
8. b, Sarkar S. K., Garigipati R. S., Adams J. L., Keifer P. A. J.Am. Chem. Soc. 1996, 118, 2305-2306.
9. 6. Look G. C., Holmes C. P., Chinn J. P., Gallop M. A. J. Org. Chem. 1994, 59, 7588-7590.
10. 7. a, Fitch W. L., Detre G., Holmes C. P., Shoolery J. N., Keifer P. A. J. Org. Chem. 1994, 59, 7955-7956.
11. b, Bayer E., Albert K., Willisch H., Rapp W., Hemmasi B. Macromolecules 1990, 23, 1937-1940.
12. 8. Anderson R. C., Jarema M. A., Shapiro M. J., Stokes J. P., Ziliox M. J. Org. Chem. 1995, 60, 2650-2651.
13. 9. Gordeev M. F., Patel D. V., Gordon E. M. J. Or. Chem. 1996, 61, 924-928.
14. 10. Experimental procedure for 3-4: The silyl ether resin (3) was produced from 1% divinyl-benzene polystyrene and dimethyldichloro silane via lithiation of the phenyl groups (Randolph J., McClure K. F., Danishefsky S. J.J. Am. Chem. Soc. 1995, 117, 5712-5719. The phenol sulfide gel (4) was produced from Merrifield resin and 4-mercapto phenol (Marshall D. L., Liener I. E. J. Org. Chem. 1970, 35, 867-868).
15. 10. Experimental procedure for 3-4: The silyl ether resin (3) was produced from 1% divinyl-benzene polystyrene and dimethyldichloro silane via lithiation of the phenyl groups (Randolph J., McClure K. F., Danishefsky S. J.J. Am. Chem. Soc. 1995, 117, 5712-5719. The phenol sulfide gel (4) was produced from Merrifield resin and 4-mercapto phenol (Marshall D. L., Liener I. E. J. Org. Chem. 1970, 35, 867-868).
16. 11. Experimental procedure for compound 5-7,9: Samples 5,6 were produced by coupling between the solid support and 9-Oxo-9H-thioxanthene-2-carboxylic acid 10,10 dioxide with water-soluble carbodiimide hydrochloride as coupling reagent and 4-pyrrolidinopyridine. Samples 7 and 9 were produced by coupling the solid support to Fmoc-Lys(Boc)-OH with water-soluble carbodiimide hydrochloride as coupling reagent and 4-pyrrolidinopyridine.
17. 3N. The liberated amine then cleaves the compound from the solid support via an intramolecular cyclization.