Orthogonally protected imidazolidine-2-carboxylic acid, a new proline surrogate suitable for SPPS

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2569-2570

  René, Loïc ^a   Yaouancq, Loïc ^a   Badet, Bernard ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; IMIDAZOLINE; TERT BUTYLOXYCARBONYL N' 9 FLUORENYLMETHYLOXYCARBONYL 2 CARBOXYLIC ACID; TERT BUTYLOXYCARCONYL N' 9 FLUORENYLMETHYLOXYCARBONYL 2 ETHYLENEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032560066     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00262-7     Document Type: Article

References (13)

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2. 2. Rivier, J.E.; Jiang, G.; Koerber, S.C.; Porter, J.; Simon, L.; Graig, A.G.; Hoeger, C.A. Proc.Natl. Acad. Sci. USA, 1996, 93, 2031-2036
3. 3. René, L.; Badet, B. Synthetic Commun. 1996, 26, 3237-3239
4. 4. Moehrle, H.; Seidel, C.M. Monatsh. Chem. 1976, 107, 51-58.
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6. 6. Watanabe, W.H. J. Am. Chem. Soc. 1957, 79, 2833-2836.
7. 3) δ 21.71, 22.18, 28.27, 28.33, 28.42, 43.61, 44.14, 45.76, 69.70, 70.56, 82.24, 169.53, 176.8; Mass spectroscopy (chemical ionization, isobutane) m/z 259 (M+H), 203 (M+H -isobuten), 159 (M+H -Boc);
8. 3) δ 28.30, 44.31, 68.11, 69.76, 82.14, 128.21, 128.65, 135.78; Mass spectroscopy (chemical ionization, isobutane) m/z 351 (M+H), 295 (M+H -isobuten), 251 (M+H -Boc).
9. 6) δ 28.42, 44.48, 47.08, 67.86, 70.16, 80.84, 120.58, 125.74, 127.69, 128.29, 141.29, 144.10, 144.16, 153.45, 170.63; Mass spectroscopy (chemical ionization, isobutane) m/z 439 (M+H), 383 (M+H -isobuten), 339 (M+H -Boc); Pentafluorophenyl ester of 3c: Mass spectroscopy (chemical ionization, isobutane) m/z 605 (M+H), 549 (M+H -isobuten), 505 (M+H -Boc).
10. 10. Barker, P.L.; Grendler, P.L.; Rapoport, H. J. Org. Chem. 1981, 46, 2455-2465.
11. 11. Adamczyk, M.; Grote, J. Org. Prep. Proceed. Int. 1995, 27, 239-342.
12. 2O, 0.05% TFA) used for purification.
13. 13. Farmerie, W.G.; Loeb, D.D.; Casavant, N.C.; Hutchinson, C.A.; Egdell, M.A.; Swanstrom, R. Science, 1987, 236, 305-308.