Process control limits from a laboratory study on the Ni(0)-mediated coupling of ethyl acrylate with a C-22 steroidal iodide: A case study on the role of experimental design in highly developed processes

Organic Process Research and Development

Volumn 8, Issue 5, 2004, Pages 769-776

  Van Arnum, Susan D ^a,c   Moffet, Harold ^a   Carpenter, Barry K ^b  

^a Pharmaceutical Research and Development   (United States)

^b Cornell University ^*  (United States)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID ETHYL ESTER; IODINE DERIVATIVE; NICKEL; NICKEL CHLORIDE; RO 251074; STEROID; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; EMPIRICISM; MATHEMATICAL ANALYSIS; PREDICTION; PROCESS CONTROL; REACTION ANALYSIS; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 5144230257     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op049908q     Document Type: Article

References (42)

1. (a) Navarrette-Bolaños, J. L.; Jiménez-Islas, H.; Botello-Alvarez, E.; Rico-Martínez, R. Org. Process Res. Dev. 2002, 6, 841-846.
2. (b) Jamieson, C.; Congreve, M. S.; Emiabata-Smith, D. F.; Ley, S. V.; Scicinski, J. J. Org. Process Res. Dev. 2002, 6, 823-825.
3. (c) Bjørsvik, H.-R.; Engell, T. Org. Process Res. Dev. 2002, 6, 113-119.
4. (d) Gavin, D. J.; Mojoca, C. A. Org. Process Res. Dev. 2001, 5, 659-664.
5. (e) Whritenour, D. C.; Brenek, S. J.; Tom, J. N. Org. Process Res. Dev. 2001, 5, 539-541.
6. (f) Higginson, P. D.; Sach, N. W. Org. Process Res. Dev. 2001, 5, 331-334.
7. (g) Hawkins, J. M.; Makowski, T. W. Org. Process Res. Dev. 2001, 5, 328-330.
8. (h) Lenderm, D.; Owen, M.; Godbert, S. Org. Process Res. Dev. 2001, 5, 324-327.
9. (i) Owen, M. R.; Luscombe, C.; Lai, L.-W.; Godbert, S.; Crookes, D. L.; Emiabata-Smith, D. Org. Process Res. Dev. 2001, 5, 308-323.
10. (j) Rosso, V. W.; Pazdan, J. L.; Venit, J. J. Org. Process Res. Dev. 2001, 5, 294-298.
11. (k) Pollard, M. Org. Process Res. Dev. 2001, 5, 273-282.
12. (l) Hermis, M. C.; Spiering, A. J. H.; Waterval, R. J. M.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Org. Process Res. Dev. 2001, 5, 54-60.
13. (m) Kirchhoff, E. W.; Anderson, D. R.; Zhang, S.; Cassidy, C. S.; Flavin, M. T. Org. Process Res. Dev. 2001, 5, 50-53.
14. (n) Simms, C.; Singh, J. Org. Process Res. Dev. 2000, 4, 545-549.
15. (o) Emiabata-Smith, D. F.; Crookes, D. L.; Owen, M. R. Org. Process Res. Dev. 1999, 3, 281-288.
16. (p) Gijsen, H. J. M.; van Bakel, H. C. C. K.; Zwaan, W.; Hulshof, L. A. Org. Process Res. Dev. 1999, 3, 38-43.
17. (q) Liu, C.; Ng, J. S.; Behling, J. R.; Yen, C. H.; Campbell, A. L.; Fuzail, K. S.; Yonan, E. E.; Mehrotra, D. V. Org. Process Res. Dev. 1997, 1, 45-54.
18. Gooding, O. W.; Vo, L.; Bhattacharyva, S.; Labadie, J. W. J. Comb. Chem. 2002, 4, 576-583.
19. Cole, D. C.; Pagano, N.; Kelly, M. F.; Ellingboe. J. Comb. Chem. 2004, 6, 78-82.
20. Deming, S. N.; Morgan, S. L. Experimental Design: A Chemometric Approach; Elsevier Science: New York, 1993.
21. Wheeler, D. J.; Chambers, D. S. Understanding Statistical Process Control; SPC Press: Knoxville, TN, 1992.
22. (a) Manchand, P. S.; Yiannikouros, G. P.; Belica, P. S.; Madan, P. J. Org. Chem. 1995, 60, 6574-6581.
23. (b) Yiannikouros, G. P.; Manchand, P. S. (Hoffmann-La Roche, Inc.). U.S. Patent 5,182,393, 1993.
24. Uskokovíc, M. R.; Barwid, T. A.; Iacobelli, J. A.; Baggiolini, E. (Hoffmann-La Roche, Inc.). U.S. Patent 3,993,675, 1975; Chem. Abstr. 1977, 86, 16846.
25. (a) For a review on the syntheses of calcitriol, see: Zhu, G.-D.; Okamura, W. H; Chem. Rev. 1995, 95, 1877-1952.
26. 3, see: Hirsch, A. L. Vitamin D. In Kirk-Othmer Encyclopedia of Chemical Technology 4th ed.; John Wiley & Sons: New York, 1998; Vol 25, pp 217-256.
27. (a) Fujiwara, A.: Miyamoto, C.; Okada, T. (Hoffmann-La Roche, Inc.). U.S. Patent 4,379, 842, 1983; Chem. Abstr. 1983, 99, 20909.
28. (b) Fujiwara, A.; Mitamoto, C.; Okada, T. (Hoffmann-La Roche, Inc.). EP 14971 A1 19800903; Chem. Abstr. 1980, 93, 236970.
29. (a) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno. J. F.; Uskokovíc, M. R. J. Org. Chem. 1986, 51, 3098-3108.
30. (b) Wovkulich, P. M.; Batcho, A. D.; Uskokovíc, M. R. Helv. Chim. Acta 1984, 67, 612-615.
31. (c) Batcho, A. D.; Uskokovíc, M. R.; Wovkulich, P. M. (Hoffmann-La Roche. Inc.). U.S. Patent 4,360,470, 1982; Chem. Abstr. 1982, 98, 143723.
32. (d) Fuerst, A.; Labler, L.; Meier, W. (Hoffmann-La Roche, Inc.). FR 2.475.557, 1981; Chem. Abstr. 1982, 96, 20379.
33. (e) Batcho, A. D.; Berger, D. E.; Davoust, S. G.; Wovkulich, P. M.; Uskokovíc, M. R. Helv. Chim. Acta 1981, 64. 1682-1687.
34. (f) Batcho, A. D.; Berger, D. E.; Uskokovíc, M. R.; Snider. B. B. J. Am. Chem. Soc. 1981, 103, 1293-1295.
35. (g) Partridge, J. J.; Uskokovíc, M. R. (Hoffmann-La Roche, Inc.). U.S. Patent 3,822.254. 1974; Chem. Abstr. 1974, 81, 78157.
36. (h) Partridge, J. J.; Faber. S.; Uskokovíc, M. R. Helv. Chim. Acta 1974, 57, 764-771.
37. 4 1118.87. MS (m/z) 1118, 1062, 986, 930 (100%), 855, 798, 724.
38. Krishnamurthy, S. J. Org. Chem. 1980, 45, 2550-2551.
39. Henningsen, M. C.; Jeropoulos, S.; Smith. E. H. J. Org. Chem. 1989, 54, 3015-3018.
40. Sustmann, R.; Hopp, P.; Holl, P. Tetrahedron Lett. 1989, 30, 689-692.
41. 2), 12.2 (C 18), 17.6 (C 21), 18.1 (C 23), 19.3 (C 19), 31.6 (C 7), 38.9 (C 2), 42.4 (C 4).
42. D.O.E. Fusion is available from S-Matrix. Corp.: 835 Third Street: Eureka, CA 95501.