By Mehdi Nafissi, John A. Ragan, Keith M. DeVries
From Bench to Pilot Plant: procedure learn within the Pharmaceutical Industry examines the bridges among learn, product improvement and production. the amount examines the move of small scale study effects to a marketable product via levels of scale up and discusses the best way to alleviate the issues of excessive expense, environmental matters, and security. Chapters contain advances in expertise of product improvement, and moving sleek examine methodologies to scale up and manufacturing.
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Distillation then afforded 2(S)-mercapto-Y-butyrolactone (19) in 70% overall yield and >97%ee. A n alternative enzymatic synthesis of 2(S)-mercapto-Y-butyrolactone (19) was also attempted as shown in Figure 8. Surprisingly, there are relatively few examples of enzymatic resolution of thiols, however, we were encouraged by the work of Cesti (16) to investigate the lipase mediated hydrolysis of racemic thioacetate 20 (9). 5: 1) 18 90%ee ^ H S < * , ^ 0 19 Reagents and conditions: (a) Mucor meihei lipase, nBuOH, toluene-FbO Figure 8.
Soc. 1992, 114, 6556. 7. Jensen, M . S . ; Yi, H . J. Organic Lett. 2000, 2, 1081-1084. 8. J. Tetrahedron Lett. 1982, 23, 2293-2296. 9. J. S. Patent 5,998,612 (1999). 10. ; Miller, R . A . ; Rossen, K . ; Reamer, R . A . ; Maliakal, A . J. J. Am. Chem. Soc. 1999, 121, 11261-11266. 11. J. 1999, 1, 17831785. ; ACS Symposium Series; American Chemical Society: Washington, DC, 2002. ch003 Matthew J. Sharp, Mark W. Andersen , Evan G. Boswell , Bobby N. Glover, Michael T. Martin, Richard T. , 5 Moore Drive, Research Triangle Park, NC 27709 - 3398 Current address: Magellan Laboratories, 160 Magellan L a b Court, Morrisville, NC 27560 Current address: Schweizerhall, 1106 Perimeter Road, Donaldson Center, Greenville, S C 29605 2 The inhaled steroid antedrug candidate GR250495X was discovered at Glaxo Wellcome for the treatment of asthma.
Ch003 Summary Four synthetic routes to the inhaled glucocorticoid antedrug candidate, GR2S0495X, were evaluated. Two of these routes were utilized to prepare significant quantities of the drug candidate. In Route 1 GR250495X was prepared in six stages and 8% overall yield from fluocinolone acetonide and the major impurity was the S-acetal derivative (5% area by H P L C ) . The key step in this route was a crystallization-induced asymmetric transformation. The major advantage of this route was that it was free of any intellectual property issues that could delay or limit the development of the drug candidate.