An Efficient Procedure for Preparation of C- and N-Protected 1-Aminocyclobutane Carboxylic Acid

Synthetic Communications

Volumn 34, Issue 4, 2004, Pages 607-613

  Kim, June J ^a   Wood, Michael R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

1 Aminocyclobutane carboxylic acid; Ethyl 1 bromocyclobutane carboxylate; Tertiary bromo esters

Indexed keywords

1 AMINOCYCLOBUTANECARBOXYLIC ACID; 1 BROMOCYCLOBUTANECARBOXYLATE; AMINO ACID; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; COST EFFECTIVENESS ANALYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 1542426189     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120027708     Document Type: Article

References (17)

1. Allan, R.D.; Hanrahan, J.R.; Hambley, T.W.; Johnston, G.A.R.; Mewett, K.N.; Mitrovic, A.D. Synthesis and activity of a potent N-methyl-D-aspartic acid agonist, trans-1-aminocyclobutane-1,3-dicarboxylic acid, and related phosphonic and carboxylic acids. J. Med. Chem. 1990, 33, 2905.
2. Gaoni, Y.; Chapman, A.G.; Parvez, N.; Pook, P.C.-K.; Jane, D.E.; Watkins, J.C. Synthesis, NMDA receptor antagonist activity, and anticonvulsant action of 1-aminocyclobutanecarboxylic acid derivatives. J. Med. Chem. 1994, 37, 4288.
3. Hanrahan, J.R.; Taylor, P.C.; Errington, W. The synthesis of 3-phosphonocyclobutyl amino acid analogues of glutamic acid via diethyl 3-oxycyclobutylphosphonate, a versatile synthetic intermediate. J. Chem. Soc. Perkin Trans. 1. 1997, 493.
4. Gershonov, E.; Granoth, R.; Tzehoval, E.; Gaoni, Y.; Fridkin, M. 1-Aminocyclobutanecarboxylic acid derivatives as novel structural elements in bioactive peptides: application to tuftsin analogs. J. Med. Chem. 1996, 39, 4833.
5. Tsang, J.W.; Schmied, B.; Nyfeler, R.; Goodman, M. Peptide sweeteners. 6. Structural studies on the C-terminal amino acid of L-aspartyl dipeptide sweeteners. J. Med. Chem. 1984, 27, 1663.
6. Gatos, M.; Formaggio, F.; Crisma, M.; Toniolo, C.; Bonora, G.M.; Benedetti, Z.; Di Blasio, B.; Iacovino, R.; Santini, A.; Saviano, M.; Kamphuis, J. Conformational characterization of the 1-aminocyclobutane-1-carboxylic acid residue in model peptides. J. Pept. Sci. 1997, 3, 110.
7. Srivastava, R.R.; Singhaus, R.R.; Kabalka, G.W. 1-Amino-3-[2-(1,7-dicarba-closo-dodecaboran(12)-1-yl)ethyl] cyclobutanecarboxylic acid: a potential BNCT agent. J. Org. Chem. 1997, 62, 4476.
8. Kalvin, D.; Ramalingam, K.; Woodard, R. A facile procedure for the preparation of alicyclic α-amino acids. Synth. Commun. 1985, 15, 267.
9. Park, K.-H.; Kurth, M.J. Diastereoselective synthesis of hydantoin- and isoxazoline-substituted dispirocyclobutanoids. J. Org. Chem. 2000, 65, 3520.
10. Gaoni, Y. Synthesis of aminocyclobutane mono- and dicarboxylic acids and derivatives thereof from (phenylsulfonyl)bicyclobutanes. Org. Prep. Proced. Int. 1995, 27, 185.
11. Corey, E.J.; Lee, D.-H.; Choi, S. An enantioselective synthesis of (2S,3S)-and (2R,3S)-3-hydroxyleucine. Tetrahedron Lett. 1992, 33, 6735.
12. Righi, G.; Rumboldt, G.; Bonini, C. A simple route to syn α-amino-β-hydroxy esters by C-2 regioselective opening of α,β-epoxy esters with metal halides. Tetrahedron 1995, 51, 13401.
13. Saito, S.; Yokoyama, H.; Ishikawa, T.; Niwa, N.; Moriwake, T. Hydrogen azide-amine systems as an azide nucleophile for substitutions of sulfonates, halides, and vicinal disulfonates. Tetrahedron Lett. 1991, 32, 663.
14. N2 displacement at tertiary carbon. Can. J. Chem. 1974, 52, 3561.
15. Watanabe, M.; Okada, H.; Teshima, T.; Noguchi, M.; Kakehi, A. A facile and regio- and stereoselective preparation of bicyclic guanidines by iodocyclization of 3-(alk-2-enyl)-2-(substituted amino)-1-imidazolin-4-ones. Tetrahedron 1996, 52, 2827.
16. Chavan, S.P.; Zubaidha, P.K.; Dhondge, V.D. A short and efficient synthesis of (-) mintlactone and (+) iso-mintlactone. Tetrahedron 1993, 49, 6429.
17. Greene, A.E.; Edgar, M.T. Synthesis of oxoisodehydroleucodin: a novel guaianolide from Montanoa imbricata. J. Org. Chem. 1989, 54, 1468.