Mild conversion of primary carboxamides into carboxylic esters

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2367-2368

  Anelli, Pier Lucio ^a   Brocchetta, Marino ^a   Palano, Daniela ^a   Visigalli, Massimo ^a  

^a Milano Research Centre   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031592601     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00350-X     Document Type: Article

References (13)

1. 1. Bobbit, J. M.; Scola, D. A. J. Org. Chem. 1960, 25, 560-564. Kumler, P. L.; Dybas, R. A. Ibid., 1970, 35, 125-131.
2. 1. Bobbit, J. M.; Scola, D. A. J. Org. Chem. 1960, 25, 560-564. Kumler, P. L.; Dybas, R. A. Ibid., 1970, 35, 125-131.
3. 2. Hamilton, D. J.; Price, M. J. J. Chem. Soc., Chem. Commun. 1969, 414.
4. 3. Greenlee, W. J.; Thorsett, E. D. J. Org. Chem. 1981, 46, 5351-5353.
5. 4. Fisher, L. E.; Caroon, J. M.; Stabler, S. R.; Lundberg, S.; Zaidi, S.; Sorensen, C. M.; Sparacino, M. L.; Muchowski, J. M. Can. J. Chem. 1994, 72, 142-145.
6. 13C NMR, MS, elemental analysis and X-ray crystal structure: Anelli, P. L.; Brocchetta, M.; Palano, D.; Paoli, P.; Visigalli, M. Book of Abstracts of the 11th ICOS, Amsterdam, The Netherlands, 30 June - 4 July 1996; Abs. PO-304.
7. 6. Use of smaller DMF-DMA/amide ratios and longer reaction times favours the formation of N,N-dimethylphenoxyacetamide. This compound is formed by reaction of 3 with dimethylamine which is generated in the cleavage of 2.
8. 13C NMR, MS and elemental analysis) in agreement with the assigned structure.
9. 8. To the best of our knowledge the only mention of a potential use of N-formylamidines as precursors of carboxylic esters is contained in: Brace, N. O. J. Org. Chem. 1993, 58, 1804-1811. N-Acylamidinium salts and suitably activated formamidines derived from secondary carboxamides have been reported to undergo alcoholysis to the corresponding alkyl carboxylates (see: Glocker, M. O.; Shrestha-Davadi, P. B.; Küchler-Krischun, J.; Hofmann, J.; Fischer, H.; Jochims, J. C. Chem. Ber. 1993, 126, 1859-1865; Ono, M.; Araya, I.; Todoriki, R.; Tamura, S. Chem. Pharm. Bull. 1990, 38, 1824-1831).
10. 8. To the best of our knowledge the only mention of a potential use of N-formylamidines as precursors of carboxylic esters is contained in: Brace, N. O. J. Org. Chem. 1993, 58, 1804-1811. N-Acylamidinium salts and suitably activated formamidines derived from secondary carboxamides have been reported to undergo alcoholysis to the corresponding alkyl carboxylates (see: Glocker, M. O.; Shrestha-Davadi, P. B.; Küchler-Krischun, J.; Hofmann, J.; Fischer, H.; Jochims, J. C. Chem. Ber. 1993, 126, 1859-1865; Ono, M.; Araya, I.; Todoriki, R.; Tamura, S. Chem. Pharm. Bull. 1990, 38, 1824-1831).
11. 8. To the best of our knowledge the only mention of a potential use of N-formylamidines as precursors of carboxylic esters is contained in: Brace, N. O. J. Org. Chem. 1993, 58, 1804-1811. N-Acylamidinium salts and suitably activated formamidines derived from secondary carboxamides have been reported to undergo alcoholysis to the corresponding alkyl carboxylates (see: Glocker, M. O.; Shrestha-Davadi, P. B.; Küchler-Krischun, J.; Hofmann, J.; Fischer, H.; Jochims, J. C. Chem. Ber. 1993, 126, 1859-1865; Ono, M.; Araya, I.; Todoriki, R.; Tamura, S. Chem. Pharm. Bull. 1990, 38, 1824-1831).
12. 9. Differently from the typical procedure (ref. 7), for the preparation of these esters it is recommended to use a 0.05-0.15 M solution of 1 in the appropriate alcohol. Under such conditions the competitive formation of the methyl ester 3 is minimized (less then 7 %).
13. 10 Abdulla, R. F.; Brinkmeyer, R. S. Tetrahedron 1979, 35, 1675-1735.