Â
A. I. Jimenez et al. / Tetrahedron 57 82001) 6019±6026
6025
Â
8. Jimenez, A. I.; Vanderesse, R.; Marraud, M.; Aubry, A.;
Cativiela, C. Tetrahedron Lett. 1997, 38, 7559±7562.
9. Burgess, K.; Ho, K.-K.; Pettitt, B. M. J. Am. Chem. Soc. 1995,
117, 54±65.
the resulting solid was washed with diethyl ether in order to
remove benzoic acid. Final lyophilization afforded pure rac-
4 as a white solid '2.25 g, 7.77 mmol, 96% yield). Mp 2048C
1
'dec.). IR 'nujol) 3600±2400, 1751, 1729 cm21. H NMR
'D2O, 300 MHz) d 3.41 'd, 1H, J8.7 Hz); 3.72'd, 1H,
J8.7 Hz); 7.20±7.44 'm, 10H). 13C NMR 'DMSO-d6,
75 MHz) d 32.71; 34.80; 44.31; 127.15; 127.81; 128.04;
128.51; 128.82; 129.95; 132.39; 134.24; 167.93. Anal.
Calcd for C16H16ClNO2: C, 66.32; H, 5.57; N, 4.83.
Found: C, 65.97; H, 5.65; N, 4.91.
10. Burgess, K.; Ho, K.-K.; Pal, B. J. Am. Chem. Soc. 1995, 117,
3808±3819.
11. Burgess, K.; Li, W.; Lim, D.; Moye-Sherman, D. Biopolymers
1997, 42, 439±453.
12. Lim, D.; Burgess, K. J. Am. Chem. Soc. 1997, 119, 9632±
9640.
13. Mapelli, C.; Stammer, C. H.; Look, S.; Mierke, D. F.;
Goodman, M. Int. J. Pept. Protein Res. 1988, 32, 484±495.
14. Mapelli, C.; Kimura, H.; Stammer, C. H. Int. J. Pept. Protein
Res. 1986, 28, 347±359.
4.9.2.
32R,3R)-1-Amino-2,3-diphenyl-1-cyclopropane-
carboxylic acid hydrochloride, 32R,3R)-4. A 3N solution
of HCl in anhydrous ethyl acetate '6 mL) was added to
'2R,3R)-5 '180 mg, 0.51 mmol) and the reaction mixture
was stirred at room temperature until completion 'ca.
30 min, TLC monitoring). After evaporation of the solvent,
the residue was taken up in water and lyophilised to afford
pure '2R,3R)-4 as a white solid '147 mg, 0.51 mmol, 100%
yield). Mp 174±1758C 'dec.). [a]D117.3 'c0.24,
MeOH). Spectroscopic data were the same as those
described for rac-4.
15. Shimohigashi, Y.; Takano, Y.; Kamiya, H.; Costa, T.; Herz,
A.; Stammer, C. H. FEBS Lett. 1988, 233, 289±293.
16. Malin, D. H.; Lake, J. R.; McDermitt, L. S.; Smith, D. A.;
Witherspoon, W. E.; Jones, J. A.; Schumann, M. D.; Payza,
K.; Ho, K.-K.; Burgess, K. Peptides 1996, 17, 83±86.
17. Malin, D. H.; Lake, R.; Payza, K.; Corriere, L. S.; Benson,
T. M.; Garber, T. L.; Waller, M. L.; Luu, T.-A.; Kelley, R. S.;
Smith, D. A.; Ho, K.-K.; Burgess, K. Peptides 1993, 14, 731±
734.
4.9.3. 32S,3S)-1-Amino-2,3-diphenyl-1-cyclopropanecar-
boxylic acid hydrochloride, 32S,3S)-4. An identical pro-
cedure to that described above was used for the conversion
of '2S,3S)-5 '138 mg, 0.39 mmol) into '2S,3S)-4 '112mg,
0.39 mmol, 100% yield). Mp 1758C 'dec.). [a]D218.8
'c0.21, MeOH). Spectroscopic data were the same as
those reported for rac-4.
18. Burgess, K.; Li, W.; Linthicum, D. S.; Ni, Q.; Pledger, D.;
Rothman, R. B.; Shitangkoon, A. Bioorg. Med. Chem. 1997, 5,
1867±1871.
Â
19. Dery, O.; Josien, H.; Grassi, J.; Chassaing, G.; Couraud, J. Y.;
Lavielle, S. Biopolymers 1996, 39, 67±74.
20. Moye-Sherman, D.; Jin, S.; Ham, I.; Lim, D.; Scholtz, J. M.;
Burgess, K. J. Am. Chem. Soc. 1998, 120, 9435±9443.
21. Moye-Sherman, D.; Jin, S.; Li, S.; Welch, M. B.; Reibenspies,
J.; Burgess, K. Chem. Eur. J. 1999, 5, 2730±2739.
5. Supporting information
Â
22. Jimenez, A. I.; Cativiela, C.; Marraud, M. Tetrahedron Lett.
2000, 41, 5353±5356.
A complete list of crystallographic data, atom coordinates,
thermal parameters, bond lengths, bond angles and torsion
angles is available from the Cambridge Crystallographic
Data Centre.
23. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem.
1985, 37, 1±109.
24. Stammer, C. H. Tetrahedron 1990, 46, 2231±2254.
25. Alami, A.; Calmes, M.; Daunis, J.; Jacquier, R. Bull. Soc.
Chim. Fr. 1993, 130, 5±24.
Acknowledgements
26. Burgess, K.; Ho, K. K.; Moye-Sherman, D. Synlett 1994, 575±
583.
This work was carried out with the ®nancial support of
Â
27. Cativiela, C.; Dõaz-de-Villegas, M. D. Tetrahedron: Asym-
metry 2000, 11, 645±732.
 Â
28. Cativiela, C.; Dõaz-de-Villegas, M. D.; Jimenez, A. I.
Tetrahedron 1994, 50, 9157±9166.
Â
Ministerio de Education y Cultura 'project PB97-0998)
and Diputacion General de Aragon 'project P22/98). The
Â
Â
Â
authors thank Dr J. A. Galvez for collecting the X-ray
data and A. L. Bernad for HPLC assistance.
Â
29. Jimenez, A. I. PhD Thesis, University of Zaragoza, 1995.
30. Rao, Y. S.; Filler, R. In Oxazolones; Turchi, I. J., Ed.; In The
Chemistry of Heterocyclic Compounds 8Weissberger, A.,
Taylor, E. C.); Wiley: New York, 1986; pp 361±691.
31. King, S. W.; Riordan, J. M.; Holt, E. M.; Stammer, C. H.
J. Org. Chem. 1982, 47, 3270±3273.
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