Preparation of clarithromycin. Selective 6-O-methylation of the novel erythromycin A 9-O-(2-pyrimidyl)oxime

Tetrahedron Letters

Volumn 48, Issue 8, 2007, Pages 1321-1324

  Brunet, Ernesto ^a   Muñoz, Dulce María ^a   Parra, Francisco ^a   Mantecón, Susana ^a   Juanes, Olga ^a   Rodríguez Ubis, Juan Carlos ^a   Carmen Cruzado, Ma ^b   Asensio, Ramón ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b Chlorine Derivatives Division   (Spain)

Author keywords

Clarithromycin; Erythromycin; Regioselective methylation

Indexed keywords

CLARITHROMYCIN; ERYTHROMYCIN; OXIME DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG QUALITY; DRUG SYNTHESIS; METHYLATION; QUALITY CONTROL;

EID: 33846345305     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.124     Document Type: Article

References (15)

1. Bermudez L.E., and Yamazaki Y. Curr. Pharm. Design 10 (2004) 3221
2. Adachi T., and Morimoto S. Macrolide Antibiot. (2002) 53
3. Liu, J.; Foster G. A., Jr.; Montgomery, S. PCT Int. Appl., 1997, 26 pp. CODEN: PIXXD2 WO 9719096 A2 19970529.
4. Asensio, R.; Cruzado, M. C.; Diaz, L. A.; Ribe, N.; Sempere, J.; Borrell, J. I. U. S. Patent Appl. Publ., 2003, 4 pp. CODEN: USXXCO US 2003023053.
5. This work is protected under patent numbers ES2221807 and JP 2005015459.
6. 3) δ (ppm): 177.6, 175.3, 165.6, 159.6, 116.4, 103.1, 96.1, 95.3, 83.6, 79.8, 77.9, 76.9, 75.0, 74.4, 72.6, 70.9, 70.0, 68.8, 65.5, 65.4, 49.4, 44.7, 40.2, 39.2, 37.7, 34.9, 34.1, 28.6, 27.9, 26.9, 21.4, 21.3, 21.2, 18.6, 18.5, 16.2, 15.9, 15.0, 13.5, 11.4, 10.6, 9.1.
7. 3) δ (ppm): 177.1, 176.0, 165.7, 159.5, 116.3, 102.7, 96.5, 81.8, 80.9, 79.3, 77.2, 77.05, 75.3, 74.5, 73.2, 73.1, 70.2, 67.7, 65.2, 65.0, 44.8, 40.9, 40.3, 38.3, 35.8, 34.3, 30.3, 29.7, 28.0, 27.0, 22.1, 21.7, 21.4, 19.2, 18.6, 16.3, 15.5, 14.9, 10.8, 9.6, 1.0, 0.8.
8. 3) δ (ppm): 176.1, 175.7, 165.9, 159.5, 116.0, 102.5, 96.2, 81.8, 80.8, 79.0, 77.7, 76.7, 75.3, 74.3, 73.3, 73.1, 70.1, 67.1, 65.2, 65.1, 50.8, 49.6, 45.2, 41.0, 39.2, 37.8, 35.8, 34.1, 31.8, 29.4, 27.8, 22.6, 22.2, 20.4, 19.4, 18.6, 16.3, 16.1, 15.1, 10.6, 9.8, 1.03, 0.84.
9. 3) δ (ppm): 176.0, 174.5, 166.2, 159.3, 115.6, 102.3, 96.3, 80.7, 79.5, 79.3, 78.2, 78.1, 77.6, 75.7, 73.2, 73.0, 67.0, 65.1, 65.0, 62.3, 50.4, 49.5, 45.1, 38.8, 37.1, 35.8, 35.7, 29.4, 27.9, 22.1, 21.9, 21.6, 20.9, 19.4, 19.3, 17.3, 16.0, 15.4, 10.5, 9.8, 1.2, 0.8.
10. CCDC 626463-626465 contains the supplementary crystallographic data for this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
11. Kawashima Y., Morimoto S., Matsunaga T., Kashimura M., Adachi T., Watanabe Y., Hatayama K., Hirono S., and Moriguchi I. Chem. Pharm. Bull. 38 (1990) 1485
12. Duran D., Aviyente V., and Baysal C. J. Comput. Mol. Design 18 (2004) 145
13. 3) δ (ppm): 175.6, 174.9, 165.8, 159.0, 115.3, 102.4, 96.4, 80.9, 80.5, 79.4, 78.3, 75.8, 72.7, 66.8, 64.9, 61.2, 53.3, 50.0, 49.3, 44.9, 40.7, 38.8, 37.2, 35.6, 29.3, 28.2, 21.8, 21.6, 19.4, 19.0, 15.8, 14.3, 10.1, 9.6, 0.6, 0.5.
14. Abuga K.O., Chepkwony H.K., Roets E., and Hoogmartens J. J. Sep. Sci. 24 (2001) 849
15. Nightingale C.H. Clin. Drug Invest. 19 (2000) 293