Synthesis of tetrazole analogs of α-amino acids by alkylation of a Schiff base of α-aminomethyltetrazole

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3367-3370

  Satoh, Yoshitaka ^a   De Lombaert, Stéphane ^a   Marcopulos, Nicholas ^a   Moliterni, John ^a   Moskal, Michael ^a   Tan, Jenny ^a   Wallace, Eli ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINOMETHYLTETRAZOLE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION;

EID: 0032554967     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00492-4     Document Type: Article

References (34)

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24. For similar alkylation reactions of stabilized Schiff bases, see: O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507-18, and references cited therein.
25. All operations involving sodium azide should be performed in a well-ventilated hood behind a blast shield.
26. The original literature procedure called for much more drastic conditions, i.e., reaction in refluxing acetic acid for several hours. See: (a) Kamiya, T., Saito, Y. US Patent 3,767,667, 1973.
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28. 4O: C, 50.32; H, 4.64; N, 23.47. Found: C, 50.64; H, 4.61; N, 23.53.
29. This seems to be a general phenomenon for the reaction with ortho esters other than orthoformates. Details will be reported elsewhere.
30. 3: C, 61.88; H, 4.32; N, 20.04. Found: C, 61.73; H, 4.20; N, 19.72.
31. 5O: C, 72.04; H, 5.52; N, 18.27. Found: C, 71.97; H, 5.49; N, 18.15.
32. 5O: C, 72.52; H, 5.83; N, 17.62. Found: C, 72.46; H, 6.04; N, 17.51.
33. In an attempt towards asymmetric synthesis of aminoalkyltetrazoles, the following chiral Schiff bases (9, 10) were prepared and subjected to alkylation with benzyl bromide. Under a variety of conditions, however, the disatereoselectivity failed to exceed - 60%. Compound 9 was prepared in a similar manner reported for the carboxylate esters (McIntosh, J. M.; Mishra, P. Can. J. Chem. 1985, 64, 726-31). Further efforts in this area will be reported in due course. (Chemical Equation Presented)
34. For a similar reaction of p-boronophenylalanine derivatives, see: Satoh, Y.; Gude, C.; Chan, K.; Firooznia, F. Tetrahedron Lett. in press.