Synthetic route for the preparation of 2-Hydroxy- N -[1-(2- hydroxyphenylamino)-1-oxoalkan-2-yl]benzamides

Journal of Combinatorial Chemistry

Volumn 12, Issue 4, 2010, Pages 414-416

  Imramovský, Aleš ^a   Férriz, Juana M ^b   Pauk, Karel ^a   Krátký, Martin ^b   Vinšová, Jarmila ^b  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

^b Charles University in Prague Faculty of Pharmacy   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZAMIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77954552350     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc900168s     Document Type: Article

References (10)

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2. Mashiko, T., Hara, K., Tanaka, D., Fujiwara, Y., Kumagai, N., and Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342-11343
3. Imramovský, A., Vinšová, J., Férriz, J. M., Buchta, V., and Jampílek, J. Bioorg. Med. Chem. Lett. 2009, 19, 348-351
4. Imramovský, A., Vinšová, J., Férriz, J. M., Doležal, R., Jampílek, J., Kaustová, J., and Kunc, F. Bioorg. Med. Chem. 2009, 17, 3572-3579
5. Waisser, K., Bureš, O., Holý, P., Kuneš, J., Oswald, R., Jirásková, L., Pour, M., Klimešová, V., Kubicová, L., and Kaustová, J. Arch. Pharm. (Weinheim, Ger.) 2003, 336, 53-71
6. Equivalent amount of substituted salicylic acid and aniline were mixed in Ph-Cl. Phosphorus trichloride (0.5 equiv) was added. The mixture was then irradiated in MW reactor MicroSynth (450W) for 20 min to reflux. Then, the reaction mixture was cooled, and the crude product collected by filtration, followed by recrystallization from acetone to obtain pure product
7. Colombo, M., Bossolo, S., and Aramini, A. J. Comb. Chem. 2009, 11, 335-337
8. General literature procedure (3b) for compound 3: N -CBZ or N -BOC protected 2-amino acid 2 (10 mmol) and substituted salicylanilide 1 (10 mmol) were dissolved in dry DMF (45 mL). The solution was cooled to -15 °C and N, N′- dicyclohexylcarbodiimide (DCC, 11 mmol) was added in three portions during 1 h. The mixture was stirred for 3 h at the same temperature and stored at +4 °C for 20 h. The precipitate of N, N′- dicyclohexylurea was removed by filtration, and the solvent was evaporated in vacuo. The crude product 3 was purified by crystallization from ethyl acetate-hexane.
9. Vinšová, J., Imramovský, A., Krátký, M., Férriz, J. M., Palát, K., Lyčka, A., and Růžička, A. Tetrahedron Lett. 2010, 51, 23-26
10. Daly, W. H. and Poché, D. Tetrahedron Lett. 1988, 29, 5859-5862