Chemoselective protection of carboxylic acid as methyl ester: A practical alternative to diazomethane protocol

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 8014-8017

  Chakraborti, Asit K ^a   Basak, Anindita ^a   Grover, Vikas ^b  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b UNIVERSITY OF BURDWAN   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; CARBOXYLIC ACID; DIAZOMETHANE; ESTER; LITHIUM; METHYL GROUP; SOLVENT;

ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CHEMICAL REACTION; ESTERIFICATION; SPECTROSCOPY;

EID: 0032723727     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990035l     Document Type: Article

References (40)

1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley: New York, 1991; 2nd ed. (b) Kocieneski, P. J. Protecting Groups; Thieme: Stuttgart, 1994.
2. (a) Sutherland I. O. Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol 2, p 871.
3. (b) Haslam, E. Tetrahedron 1980,36, 2409.
4. Ladduwahettu, T. Contemp. Org. Synth. 1997, 4, 326.
5. (a) Nayak, M. K; Chakraborti, A. K. Chem. Lett. 1998, 297.
6. (b) Mascaretti, O. A.; Furlane, R. L. E. Aldrichimica Acta 1997, 30, 55.
7. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron 1993, 49, 3691.
8. McMurry, J. E. Org. React. 1976, 24, 187.
9. (e) Muller, P.; Siegfried, B. Helv. Chim. Acta. 1974, 57, 987.
10. March, J. Advanced Organic Chemistry; Wiley Eastern Limited: New Delhi, 1992.
11. Furniss, B. R.; Hannaford, A. J.; Rogers, V.; Smith, P. AV. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Longman: London, 1996.
12. Denney, D. B.; Meli, R.; Pendse, A. D. J. Org. Chem. 1978, 43, 4672.
13. Yamauchi, K; Tanabe, T.; Kinoshita, M. J. Org. Chem. 1979, 44, 638.
14. (a) Pfister, J. R.; Wyman, W. E.; Mahoney, J. M.; Waterbury, L. D. J. Med. Chem. 1980, 23, 1264.
15. (b) Ballini, R.; Carotti, A. Synth. Commun. 1983, 13, 1197.
16. Shoda, S.; Mukaiyama, T. Chem. Lett. 1980, 391.
17. Mohacsi, E. Synth. Commun. 1982, 12, 453.
18. Badet, B.; Julia, M.; Ramirez-Munoz, M.; Sarrazin, C. A. Tetrahedron 1983, 39, 3111.
19. Renga, J. M.; Wang, P.-C. Synth. Commun. 1984, 14, 77.
20. Krutius, O.; Eremeev, A. V. Chem. Abstr. 1989,110, 114583n.
21. Sato, T.; Otera, J.; Nazaki, H. J. Org. Chem. 1992, 57, 2166.
22. Puntambekar, H. M.; Naik, D. G.; Kapadi, A. H. Indian J. Chem., Sect. B 1993, 32B, 793.
23. Uchama, S.; Nakano, R.; Machida, H. Chem. Abstr. 1995, 723, 9171x.
24. (a) Bhatia, V. G.; Shaikh, A. S.; Tongare, D. B.; Balasubramaniyan, V. Indian J. Chem., Sect. B 1982, 21B, 259.
25. (b) Rao, A. V. R.; Deshmukh, M. N.; Sivadasan, L. Chem. Ind. (London) 1981, 164.
26. Jamieson, N. C.; Loncrini, D. F. Chem. Ind. (London) 1979, 522.
27. (a) Ho, G.-J.; Mathre, D. J. J. Org. Chem. 1995, 60, 2271.
28. (b) Hoobler, M. A.; Bergbreiter, D. E.; Newcomb, M. J. Am. Chem. Soc. 1978, 700, 8182.
29. Meyers, A. L; Snyder, E. S.; Ackerman, J. J. H. J. Am. Chem. Soc. 1978, 700, 8186.
30. Basak, A.; Nayak, M. K; Chakraborti, A. K. Tetrahedron Lett. 1998, 39, 4883.
31. 1H NMR and GO-MS spectra of the crude products corresponding to entries 5,11,12, and 26 did not show any methylation of the phenolic hydroxyl group.
32. (a) Bisarya, S. C.; Rao, R. Synth. Commun. 1992,22, 3305. (b) Sukata, K. Bull. Chem. Soc. Jpn. 1985, 58, 838. (c) Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169.
33. Julia, M.; Mestdach, H. Tetrahedron 1983, 39, 433.
34. The methyl ester of the corresponding unprotected amino acids could not be made with this protocol as the amino acids are insoluble in THF.
35. The methyl esters of optically pure acids 1, 4, and 5 were obtained in >98% ee as determined by the 1H NMR spectra in the presence of Eu(hfc)2.
36. Chevallet, P.; Fehrentz, J.-A.; Kiec-Kononowicz, K.; Devin, C.; Castel, J.; Loffet, A.; Martinez, J. Lett. Pept. Sci. 1996, 2, 297.
37. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
38. Shinkai, S.; Fukunaga, T.; Manabe, O.; Kunitake, T. J. Org. Chem. 1979, 44, 4990.
39. (a) Weast, R. C. Handbook of Chemistry and Physics; CRC: Cleveland, 1987-88; 68th ed.; (b) Gladilovich, D. B.; Grigor'ev, N. N.; Stolyarov, K. P. Chem. Abstr. 1977, 88, 66457c.
40. Grundy, J.; James, B. G.; Pattenden G. Tetrahedron Lett. 1972, 757.