Preparation of amides from acids and resin bound azides: Suppression of intramolecular lactam formation

Tetrahedron Letters

Volumn 39, Issue 27, 1998, Pages 4773-4776

  Tang, Zhilian ^a   Pelletier, Jeffrey C ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; AMIDE; AZIDE; LACTAM DERIVATIVE; RESIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS;

EID: 0032474786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00905-8     Document Type: Article

References (16)

1. [1] Hermkens PHH, Ottenheijm HCJ, Rees DC. Tetrahedron 1997; 53: 5643-5678. Hermkens PHH, Ottenheijm HCJ, Rees DC. Tetrahedron 1996; 52: 4527-4552.
2. [1] Hermkens PHH, Ottenheijm HCJ, Rees DC. Tetrahedron 1997; 53: 5643-5678. Hermkens PHH, Ottenheijm HCJ, Rees DC. Tetrahedron 1996; 52: 4527-4552.
3. [2] Merrifield RB. J. Am. Chem. Soc. 1963; 85: 2149-2154.
4. [3] Carpino LA, Han GY. J. Org. Chem. 1972; 37: 3404-3409. Atherton E, Sheppard RC. Solid Phase Peptide Synthesis, a Practical Approach. Rickwood D, Hames BD, Eds. Oxford: IRL Press, 1989.
5. [3] Carpino LA, Han GY. J. Org. Chem. 1972; 37: 3404-3409. Atherton E, Sheppard RC. Solid Phase Peptide Synthesis, a Practical Approach. Rickwood D, Hames BD, Eds. Oxford: IRL Press, 1989.
6. 13C-NMR and IR analyses. Solid phase yields are based on gravimetric analysis and comparison to the manufacturers suggested loading levels.
7. [5] Wang SS. J. Am. Chem. Soc. 1973; 95: 1328-1333.
8. [6] Lactam 7 was prepared independently from the following route and used as a standard for comparison purposes: (equation presented)
9. [7] Rosen T, Lico IM, Chu DTW. J. Org. Chem. 1988; 53: 1580-1582. Ghosh SK, Singh U, Mamdapur VR. Tetrahedron Lett. 1992; 33: 805-808. Zaloom J, Calandra M, Roberts DC. J. Org. Chem. 1985; 50: 2601-2603.
10. [7] Rosen T, Lico IM, Chu DTW. J. Org. Chem. 1988; 53: 1580-1582. Ghosh SK, Singh U, Mamdapur VR. Tetrahedron Lett. 1992; 33: 805-808. Zaloom J, Calandra M, Roberts DC. J. Org. Chem. 1985; 50: 2601-2603.
11. [7] Rosen T, Lico IM, Chu DTW. J. Org. Chem. 1988; 53: 1580-1582. Ghosh SK, Singh U, Mamdapur VR. Tetrahedron Lett. 1992; 33: 805-808. Zaloom J, Calandra M, Roberts DC. J. Org. Chem. 1985; 50: 2601-2603.
12. [8] Bosch I, Romea P, Urpi F, Vilarrasa J. Tetrahedron Lett. 1993; 34: 4671-4674.
13. [9] Collini MD, Ellingboe JW. Tetrahedron Lett. 1997; 38: 7963-7966.
14. [10]Acid 9 and the starting acids from entries 1 & 2 in the table are available commercially from Neosystem Laboratoire, Strasbourg, FR.
15. 6) δ 8.40 (t, 1H, J = 3.3 Hz), 7.90 (d, 2H, J = 7.4), 7.80-7.65 (m, 3H), 7.43-6.90 (m, 10H), 5.05 (d, 2H, J = 8.5), 4.39-4.13 (m, 3H), 3.63 (S, 2H), 3.46 (dd, 1H, J = 28 Hz, J = 11.6), 3.07-2.89 (m, 3H), 2.23-2.05 (m, 2H), 1.38 (bs, 1H), 0.88 (t, 1H, J = 3.5 Hz).
16. [12]Goff DA, Zuckerman RN. J. Org. Chem. 1995; 60: 5744-5745.