Sulfonation with inversion by Mitsunobu reaction: An improvement on the original conditions

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7955-7958

  Anderson, Neal G ^a   Lust, David A ^a   Colapret, Kay A ^a,b   Simpson, James H ^a   Malley, Mary F ^a   Gougoutas, Jack Z ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b Texaco Inc Bellaire   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001125915     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609539     Document Type: Article

References (51)

1. (a) Galynker, I.; Still, W. C. Tetrahedron Lett. 1982, 23, 4461.
2. For scope and mechanistic details on the Mitsunobu reaction, see: (b) Mitsunobu, O. Synth. 1981, 1, 1. (c) Hughes, D. L. The Mitsunobu Reaction. Organic Reactions; John Wiley and Sons, Inc.: 1992; Vol. 42, p 335. (d) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487. (e) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 129. (f) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
3. For scope and mechanistic details on the Mitsunobu reaction, see: (b) Mitsunobu, O. Synth. 1981, 1, 1. (c) Hughes, D. L. The Mitsunobu Reaction. Organic Reactions; John Wiley and Sons, Inc.: 1992; Vol. 42, p 335. (d) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487. (e) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 129. (f) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
4. For scope and mechanistic details on the Mitsunobu reaction, see: (b) Mitsunobu, O. Synth. 1981, 1, 1. (c) Hughes, D. L. The Mitsunobu Reaction. Organic Reactions; John Wiley and Sons, Inc.: 1992; Vol. 42, p 335. (d) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487. (e) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 129. (f) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
5. For scope and mechanistic details on the Mitsunobu reaction, see: (b) Mitsunobu, O. Synth. 1981, 1, 1. (c) Hughes, D. L. The Mitsunobu Reaction. Organic Reactions; John Wiley and Sons, Inc.: 1992; Vol. 42, p 335. (d) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487. (e) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 129. (f) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
6. For scope and mechanistic details on the Mitsunobu reaction, see: (b) Mitsunobu, O. Synth. 1981, 1, 1. (c) Hughes, D. L. The Mitsunobu Reaction. Organic Reactions; John Wiley and Sons, Inc.: 1992; Vol. 42, p 335. (d) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487. (e) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 129. (f) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
7. (a) Emmer, G.; Grassberger, M. A.; Meingassner, J. G.; Schulz, G.; Schaude, M. J. Med. Chem. 1994, 37, 1908.
8. (b) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Org. Chem. 1992, 57, 3631.
9. (c) Ladouceur, G.; Mais, D. E.; Jakubowski, J. A.; Utterback, B. G.; Robertson, D. W. Biomed. Lett. 1991, 1, 173.
10. (d) Salomon, R. G.; Basu, B.; Roy, S.; Sachinvala, N. D. J. Am. Chem. Soc. 1991, 113, 3096.
11. (e) Iguchi, S.; Miyata, Y.; Miyake, H.; Arai, Y.; Okegawa, T.; Kawasaki, A. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 1989, 19, 670.
12. (f) Thierauch, K. H.; Sturzebecher, C. S.; Schillinger, E.; Rehwinkel, H.; Raduchel, B.; Skuballa, W.; Vorbruggen, H. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 1989, 19, 655.
13. (g) Thierauch, K. H.; Sturzebecher, C. S.; Schillinger, E.; Rehwinkel, H.; Raduchel, B.; Skuballa, W.; Vorbruggen, H. Prostaglandins 1988, 35, 855.
14. (h) Iguchi, S.; Miyata, Y.; Okuyama, S.; Miyake, H.; Okegawa, T. Chem. Pharm. Bull. 1988, 36, 1128.
15. (i) Mori, K.; Kuwahara, S. Liebigs Ann. Chem. 1987, 6, 555.
16. (j) Pougny, J. R.; Rollin, P. J. Carbohydr. Chem. 1986, 5, 701.
17. (k) Falck, J. R.; Manna, S.; Capedevila, J. Tetrahedron Lett. 1984, 25, 2443.
18. (l) Laesecke, K.; Kohn, A.; Schmidt, R. R. Liebigs Ann. Chem. 1983, 1429.
19. (a) Pianetti, P.; Rollin, P.; Pougny, J. R. Tetrahedron Lett. 1986, 27, 5853.
20. (b) Rollin, P. Synth. Commun. 1986, 16, 611.
21. (c) Ho, P. T.; Davies, N. J. Org. Chem. 1984, 49, 3027.
22. For examples, see: (a) Smith, A. B., III; Hale, K. J.; Rivero, R. A. Tetrahedron Lett. 1986, 27, 5813. (b) Bowers-Nemia, M. M.; Joullié, M. M. Heterocycles 1983, 20, 817. Preparing the lactone from the carboxylic acid precursor of 1 would have added another step to the sequence.
23. For examples, see: (a) Smith, A. B., III; Hale, K. J.; Rivero, R. A. Tetrahedron Lett. 1986, 27, 5813. (b) Bowers-Nemia, M. M.; Joullié, M. M. Heterocycles 1983, 20, 817. Preparing the lactone from the carboxylic acid precursor of 1 would have added another step to the sequence.
24. The product has also been removed by pH-controlled extraction from the Mitsunobu byproducts: King, M. L.; Forman, A. L.; Orella, C.; Pines, S. H. Chem. Eng. Prog. 1985, 36.
25. Krapcho, J.; Turk, C.; Cushman, D. W.; Powell, J. R.; DeForrest, J. M.; Spitzmiller, E. R.; Karanewsky, D. S.; Duggan, M.; Rovnyak, G.; Schwartz, J.; Natarajan, S.; Godfrey, J. D.; Ryono, D. E.; Neubeck, R.; Atwal, K. S.; Petrillo, E. W., Jr. J. Med. Chem. 1988, 31, 1148.
26. (a) Kronenthal, D. R.; Mueller, R. H.; Kuester, P. L.; Kissick, T. P.; Johnson, E. J. Tetrahedron Lett. 1990, 31, 1241.
27. (b) Kronenthal, D.; Kuester, P. L.; Mueller, R. H. U.S. Pat. 4912231.
28. Georges, M.; Mackay, D.; Fraser-Reid, B. Can. J. Chem. 1984, 62, 1539.
29. For a discussion on safety considerations of azodicarboxylates, see: Org. Synth. 1995, 73, 278.
30. Small amounts of the 3,4- and 4,5-dehydroproline impurities were detected, along with impurities similar to compound 4 in ref 1a.
31. Refluxing overnight decreased the ratio to ca. 92:8, probably due to epimerization a to the methyl ester. The absolute stereochemistry of the trans-mesylate ester detected in this Mitsunobu reaction is not known.
32. Conducting the Mitsunobu reaction in toluene probably promotes the crystallization of the complex, as toluene has been shown to be a suitable solvent for crystallization of weakly acidic compounds with triphenylphosphine oxide: Etter, M. C; Baures, P. W. J. Am. Chem. Soc. 1988, 110, 639.
33. Coordinates for the X-ray determinations have been deposited in the Cambridge Crystallographic Database and can be obtained upon request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
34. Shamala, N.; Row, T. N. G.; Venkatesan, K. Acta Crystallogr., B 1976, 32, 3267 (AHLPRO). All referenced crystal structures were retrieved from the Cambridge Structural Database, April 1996 release (CSD: Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F., Mitchell, E. M.; Mitchell, G.F.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comp. Sci. 1991, 31, 187-204). CSD refcodes are included at the end of each reference.
35. Shamala, N.; Row, T. N. G.; Venkatesan, K. Acta Crystallogr., B 1976, 32, 3267 (AHLPRO). All referenced crystal structures were retrieved from the Cambridge Structural Database, April 1996 release (CSD: Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F., Mitchell, E. M.; Mitchell, G.F.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comp. Sci. 1991, 31, 187-204). CSD refcodes are included at the end of each reference.
36. Palkowitz, A. D.; Steinberg, M. I.; Thrasher, K. J.; Reel, J. K.; Hauser, K L.; Zimmerman, K. M.; Wiest, S. A.; Whitesitt, C. A.; Simon, R. L.; Pfeifer, W.; Lifer, S. L.; Boyd, D. B.; Barnett, C. J.; Wilson, T. M.; Deeter, J. B.; Takeuchi, K.; Riley, R.E.; Miller, W. D.; Marshall, W. S. J. Med. Chem. 1994 37, 4508 (YIHJEE).
37. Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009 (TALBUD).
38. Cerrini, S.; Lamba, D.; Scatturin, A.; Rossi, C.; Ughetto, G. Biopolymers 1989, 28, 409 (JATZIN).
39. Flippen-Anderson, J. L.; Gilardi, R.; Karle, I. L.; Frey, M. H.; Opella, S. J.; Gierasch, L. M.; Goodman, M.; Madison, V.; Delaney, N. G. J. Am. Chem. Soc. 1983, 105, 6609 (CEDREI and CEDRAE).
40. Yanagi, K.; Takeuchi, Y.; Sunagawa, M. Acta Crystallogr., Sect. C 1992, 48, 1737 (VUCJEI).
41. Leban, I.; Golic, L.; Resman, A.; Zmitek, J. Acta Chim. Slav. 1994, 41, 405 (SUPBIO).
42. Dupont, L.; Lamotte, J.; Campsteyn, H.; Vermeire, M.; Welter, A. Acta Crystallogr., Sect. B 1978, 34, 850 (CXPROL).
43. Bernardinelli, G.; Tronchet, J. M. J.; Jorand, C. Z. Kristallogr. 1991, 195, 129 (SIYYOO).
44. Seven of eight such trans-4-hydroxyproline structures have an axial OH (e.g. Koetzle, T. F.; Lehmann, M. S.; Hamilton, W. C. Acta Crystallogr., Sect. B 1973, 29, 231 (HOPROL12). Hospital, M.; Courseille, C.; Leroy, F.; Roques, B. P. Biopolymers, 1979, 18, 1141 (NAHYPL, or N-acetyl-trans-4-hydroxyproline). Garbay-Jaureguiberry, C.; Arnoux, B.; Prange, T.; Wehri-Altenburger, S.; Pascard, C.; Roques, B. P. J. Am. Chem. Soc. 1980, 102, 1827 (GLHPRC, or prolylhydroxyproline)). The last reference also contains the exception: the hydroxyl is pseudoequatorial in glycyl-L-4-hydroxyproline (GLHPRA). Intermediate conformations occur in two mono- and di-N-alkylated derivatives: Jones, G. P.; Naidu, B. P.; Paleg, L. G.; Tiekink, E. R. T. Acta Crystallogr. Sect. C 1988, 44, 2208 (GOJMAT and GOJMEX).
45. Seven of eight such trans-4-hydroxyproline structures have an axial OH (e.g. Koetzle, T. F.; Lehmann, M. S.; Hamilton, W. C. Acta Crystallogr., Sect. B 1973, 29, 231 (HOPROL12). Hospital, M.; Courseille, C.; Leroy, F.; Roques, B. P. Biopolymers, 1979, 18, 1141 (NAHYPL, or N-acetyl-trans-4-hydroxyproline). Garbay-Jaureguiberry, C.; Arnoux, B.; Prange, T.; Wehri-Altenburger, S.; Pascard, C.; Roques, B. P. J. Am. Chem. Soc. 1980, 102, 1827 (GLHPRC, or prolylhydroxyproline)). The last reference also contains the exception: the hydroxyl is pseudoequatorial in glycyl-L-4-hydroxyproline (GLHPRA). Intermediate conformations occur in two mono- and di-N-alkylated derivatives: Jones, G. P.; Naidu, B. P.; Paleg, L. G.; Tiekink, E. R. T. Acta Crystallogr. Sect. C 1988, 44, 2208 (GOJMAT and GOJMEX).
46. Seven of eight such trans-4-hydroxyproline structures have an axial OH (e.g. Koetzle, T. F.; Lehmann, M. S.; Hamilton, W. C. Acta Crystallogr., Sect. B 1973, 29, 231 (HOPROL12). Hospital, M.; Courseille, C.; Leroy, F.; Roques, B. P. Biopolymers, 1979, 18, 1141 (NAHYPL, or N-acetyl-trans-4-hydroxyproline). Garbay-Jaureguiberry, C.; Arnoux, B.; Prange, T.; Wehri-Altenburger, S.; Pascard, C.; Roques, B. P. J. Am. Chem. Soc. 1980, 102, 1827 (GLHPRC, or prolylhydroxyproline)). The last reference also contains the exception: the hydroxyl is pseudoequatorial in glycyl-L-4-hydroxyproline (GLHPRA). Intermediate conformations occur in two mono- and di-N-alkylated derivatives: Jones, G. P.; Naidu, B. P.; Paleg, L. G.; Tiekink, E. R. T. Acta Crystallogr. Sect. C 1988, 44, 2208 (GOJMAT and GOJMEX).
47. Seven of eight such trans-4-hydroxyproline structures have an axial OH (e.g. Koetzle, T. F.; Lehmann, M. S.; Hamilton, W. C. Acta Crystallogr., Sect. B 1973, 29, 231 (HOPROL12). Hospital, M.; Courseille, C.; Leroy, F.; Roques, B. P. Biopolymers, 1979, 18, 1141 (NAHYPL, or N-acetyl-trans-4-hydroxyproline). Garbay-Jaureguiberry, C.; Arnoux, B.; Prange, T.; Wehri-Altenburger, S.; Pascard, C.; Roques, B. P. J. Am. Chem. Soc. 1980, 102, 1827 (GLHPRC, or prolylhydroxyproline)). The last reference also contains the exception: the hydroxyl is pseudoequatorial in glycyl-L-4-hydroxyproline (GLHPRA). Intermediate conformations occur in two mono- and di-N-alkylated derivatives: Jones, G. P.; Naidu, B. P.; Paleg, L. G.; Tiekink, E. R. T. Acta Crystallogr. Sect. C 1988, 44, 2208 (GOJMAT and GOJMEX).
48. DIAD purity may be determined by dissolving a standardized amount of triphenylphosphine in acetonitrile containing 0.2% acetic acid and titrating with DIAD until the yellow-orange color remains.
49. Portoghese, P. S.; Turcotte, J. G. Tetrahedron 1971, 27, 961. The ester was dried to moisture levels of not more than 0.1%.
50. 4), 215 nm. Typical retention times: 1, 10.4 min; 2, 16.7 min; 3, 7.6 min; 4, 18.0 min; 5, 8.0 min.
51. YMC Basic 25 cm column, eluted at 1.0 mL/min with 50:50 acetonitrile:0.01 M ammonium phosphate, acidified to pH 4 after mixing, monitored at 210 nm. Typical retention times: 1, 3.7 min; ester intermediate, 8.5 min; 6, 5.6 min.