Studies on the Synthesis of cis-4-Hydroxy-l-proline
Jessica A. Smith A , G. Paul Savage A and Oliver E. Hutt A B
+ Author Affiliations
- Author Affiliations
A Ian Wark Laboratory, CSIRO Materials Science and Engineering, Bag 10, Clayton South MDC, Vic. 3169, Australia.
B Corresponding author. Email: oliver.hutt@csiro.au
Australian Journal of Chemistry 64(11) 1509-1514 https://doi.org/10.1071/CH11204
Submitted: 20 May 2011 Accepted: 28 July 2011 Published: 16 November 2011
Abstract
A high yielding practical three-step procedure, which relies on an extractive work-up procedure, has been developed to convert N-phenylsulfonyl-trans-4-hydroxy-l-proline to N-phenylsulfonyl-cis-4-hydroxy-l-proline methyl ester in 82 % yield over three steps.
References
[1] M. T. Rudd, J. A. McCauley, J. W. Butcher, J. J. Romano, C. J. McIntyre, K. T. Nguyen, K. F. Gilbert, K. J. Bush, M. K. Holloway, J. Swestock, B.-L. Wan, S. S. Carroll, J. M. DiMuzio, D. J. Graham, S. W. Ludmerer, M. W. Stahlhut, C. M. Fandozzi, N. Trainor, D. B. Olsen, J. P. Vacca, N. J. Liverton, ACS Med. Chem. Lett. 2011, 2, 207.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXksFCitA%3D%3D&md5=7c40b60b8073c692ab50ec9581e72708CAS |
[2] J. A. Butera, B. D. Larsen, J. K. Hennan, E. Kerns, L. Di, A. Alimardanov, R. E. Swillo, G. A. Morgan, K. Liu, Q. Wang, E. I. Rossman, R. Unwalla, L. McDonald, C. Huselton, J. S. Petersen, J. Med. Chem. 2009, 52, 908.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1Ogu7o%3D&md5=14d9d9332078c8a8d0401358c68a754eCAS |
[3] M. G. Natchus, R. G. Bookland, B. De, N. G. Almstead, S. Pikul, M. J. Janusz, S. A. Heitmeyer, E. B. Hookfin, L. C. Hsieh, M. E. Dowty, C. R. Dietsch, V. S. Patel, S. M. Garver, F. Gu, M. E. Pokross, G. E. Mieling, T. R. Baker, D. J. Foltz, S. X. Peng, D. M. Bornes, M. J. Strojnowski, Y. O. Taiwo, J. Med. Chem. 2000, 43, 4948.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXnvVKht7o%3D&md5=6809fe9a75e5fe23caa8b3e3af7ab97cCAS |
[4] A. A. Patchett, B. Witkop, J. Am. Chem. Soc. 1957, 79, 185.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG2sXjsVyjsw%3D%3D&md5=518cc4ea9c818d12b611d1dcc8ec7702CAS |
[5] H. Bernard, G. Bulow, U. E. W. Lange, H. Mack, T. Pfeiffer, B. Schafer, W. Seitz, T. Zierke, Synthesis 2004, 2367.
| 1:CAS:528:DC%2BD2cXosVyqurk%3D&md5=b9555ed0346efde5e2a0817bbc2d5dacCAS |
[6] M. S. Chorghade, D. K. Mohapatra, G. Sahoo, M. K. Gurjar, M. V. Mandlecha, N. Bhoite, S. Moghe, R. T. Raines, J. Fluor. Chem. 2008, 129, 781.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVyitrbM&md5=3f0e721ee8b6addb28a044e4fcc26aaaCAS |
[7] P. S. Portoghese, A. A. Mikhail, J. Org. Chem. 1966, 31, 1059.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF28XnsFOguw%3D%3D&md5=2f64dc97f3aada55c617ad2041333d47CAS |
[8] R. H. Andreatta, V. Nair, A. V. Robertson, W. R. J. Simpson, Aust. J. Chem. 1967, 20, 1493.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2sXltFOht7o%3D&md5=ab960c31b10bb1e35f3b9e0196c450c3CAS |
[9] M. M. Bowers-nemia, M. M. Joullié, Heterocycles 1983, 20, 817.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXlsVSgs7k%3D&md5=42f6bd50fdd63dd7aa301cae91bf50caCAS |
[10] P. Dalla Croce, C. La Rosa, Tetrahedron Asymmetry 2002, 13, 197.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XitlWhur4%3D&md5=8f4089d2af41ae31f3ffcdaddf6d17d2CAS |
[11] N. G. Anderson, D. A. Lust, K. A. Colapret, J. H. Simpson, M. F. Malley, J. Z. Gougoutas, J. Org. Chem. 1996, 61, 7955.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XmtFyqtrc%3D&md5=f96ed2b8c569d2a95c438cb8c4559421CAS |
[12] D. J. Pippel, L. K. Young, M. A. Letavic, K. S. Ly, B. Naderi, A. Soyode-Johnson, E. M. Stocking, N. I. Carruthers, N. S. Mani, J. Org. Chem. 2010, 75, 4463.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntFyqur4%3D&md5=034a382616094fcb075f883db71599ebCAS |
[13] J. A. Gómez-Vidal, R. B. Silverman, Org. Lett. 2001, 3, 2481.
| Crossref | GoogleScholarGoogle Scholar |
[14] A. V. Thomas, H. H. Patel, L. A. Reif, S. R. Chemburkar, D. P. Sawick, B. Shelat, M. K. Balmer, R. R. Patel, Org. Process Res. Dev. 1997, 1, 294.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXks1Cqu74%3D&md5=be295e5b1094239f1377740ffd795463CAS |
[15] A. M. Palmer, M. Webel, C. Scheufler, D. Haag, B. Muller, Org. Process Res. Dev. 2008, 12, 1170.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFKlurzP&md5=b7a54d44f725367c097b1e813a8a1d9bCAS |
[16] H. B. Milne, C.-H. Peng, J. Am. Chem. Soc. 1957, 79, 639.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG2sXls1Crtg%3D%3D&md5=5dd362f7121d4e6a2da93017381018feCAS |
[17] R. Melgar-Fernández, R. González-Olvera, J. L. Olivares-Romero, V. González-López, L. Romero-Ponce, M. R. Ramírez-Zárate, P. Demare, I. Regla, E. Juaristi, Eur. J. Org. Chem. 2008, 2008, 655.
| Crossref | GoogleScholarGoogle Scholar |
[18] J. A. Gómez-Vidal, M. T. Forrester, R. B. Silverman, Org. Lett. 2001, 3, 2477.
| Crossref | GoogleScholarGoogle Scholar |
[19] D. Papaioannou, G. Stavropoulos, K. Karagiannis, G. W. Francis, T. Brekke, D. W. Aksnes, Acta Chem. Scand. 1990, 44, 243.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXlsFejs7o%3D&md5=1d4e040a8dde5218955d6329d0ec2b50CAS |
[20] H. Mues, U. Kazmaier, Synthesis 2001, 0487.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhvVKmsrw%3D&md5=8615227230da42831ebe6264f093f580CAS |
[21] S. Stamm, H. Heimgartner, Helv. Chim. Acta 2006, 89, 1841.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFSisbnN&md5=001ba6bae974344a7a15ac4d2dd28030CAS |
[22] R. H. Andreatta, V. Nair, A. V. Robertson, Aust. J. Chem. 1967, 20, 2701.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXhtFygtLo%3D&md5=e45f7098f5cee7021e12deeb932830efCAS |
