Use of pentafluorophenyl esters for one-pot protection/activation of amino and thiol carboxylic acids

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4915-4918

  Gayo, Leah M ^a   Suto, Mark J ^a  

^a CELGENE CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; N,N DIMETHYLFORMAMIDE; PYRIDINE DERIVATIVE; REAGENT; THIOL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CRYSTALLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0030575382     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00985-9     Document Type: Article

References (13)

1. 1. Boojamra, C. G., Burrow, K. M., Ellman, J. A. J. Org. Chem., 1995, 60, 5742; Thompson, L. A., Ellman, J. A. Chem. Rev., 1996, 96, 555; Bunin, B. A., Plunkett, M. J., Ellman, J. A. Proc. Natl. Acad. Sci. USA, 1994, 91, 4708.
2. 1. Boojamra, C. G., Burrow, K. M., Ellman, J. A. J. Org. Chem., 1995, 60, 5742; Thompson, L. A., Ellman, J. A. Chem. Rev., 1996, 96, 555; Bunin, B. A., Plunkett, M. J., Ellman, J. A. Proc. Natl. Acad. Sci. USA, 1994, 91, 4708.
3. 1. Boojamra, C. G., Burrow, K. M., Ellman, J. A. J. Org. Chem., 1995, 60, 5742; Thompson, L. A., Ellman, J. A. Chem. Rev., 1996, 96, 555; Bunin, B. A., Plunkett, M. J., Ellman, J. A. Proc. Natl. Acad. Sci. USA, 1994, 91, 4708.
4. 2. Kisfauldy, L., Schon, I. Synthesis, 1983, 325; Adamczyk, M., Johnson, D. OPPI Briefs, 1993, 25(5), 592; Schmidt, U., Utz., R. Angew Chem, 1984, 96(9), 723.
5. 2. Kisfauldy, L., Schon, I. Synthesis, 1983, 325; Adamczyk, M., Johnson, D. OPPI Briefs, 1993, 25(5), 592; Schmidt, U., Utz., R. Angew Chem, 1984, 96(9), 723.
6. 2. Kisfauldy, L., Schon, I. Synthesis, 1983, 325; Adamczyk, M., Johnson, D. OPPI Briefs, 1993, 25(5), 592; Schmidt, U., Utz., R. Angew Chem, 1984, 96(9), 723.
7. 3. Green, M., Berman, J. Tetrahedron Lett., 1990, 31, 5851.
8. 4. Kisfauldy, L., Mohacsi, T., Low, M., Drexler, F. J. Org. Chem., 1979, 44, 654; Schon, I., Kisfauldy, L. Synthesis, 1986, 303; Breslav, M.S., Kalejs, U.; Pupikina, S.; Doviborov, N. J. Chem. Research, 1992, 272.
9. 4. Kisfauldy, L., Mohacsi, T., Low, M., Drexler, F. J. Org. Chem., 1979, 44, 654; Schon, I., Kisfauldy, L. Synthesis, 1986, 303; Breslav, M.S., Kalejs, U.; Pupikina, S.; Doviborov, N. J. Chem. Research, 1992, 272.
10. 4. Kisfauldy, L., Mohacsi, T., Low, M., Drexler, F. J. Org. Chem., 1979, 44, 654; Schon, I., Kisfauldy, L. Synthesis, 1986, 303; Breslav, M.S., Kalejs, U.; Pupikina, S.; Doviborov, N. J. Chem. Research, 1992, 272.
11. 3) δ 8.17 (d, 2H), 7.25 (d, 2H), 4.35 (s, 2H) ); m.p 47-49 °C.
12. 6. Daines, R. A., Chambers, P. A., Drake, S. E., Foley, J. J., Griswold, D. E., Haltiwanger, R. C., Jakas, D. R., Kingsbury, W. D., Martin, L. D., Pendrak, I., Schmidt, D. B., Tzimas, M. N., Sarau, H. M. J. Med. Chem., 1994, 37, 3327.
13. 2, piperidine) to provide the corresponding N-trifluoroacetyl amides in >85% yields after aqueous workup. (formula presented)