Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The “DCAT Route” to thiophenesulfonamides

…, AP Dantanarayana, MT DuPriest

文献索引：Conrow, Raymond E.; Dean, W. Dennis; Zinke, Paul W.; Deason, Michael E.; Sproull, Steven J.; Dantanarayana, Anura P.; DuPriest, Mark T. Organic Process Research and Development, 1999 , vol. 3, # 2 p. 114 - 120

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被引用次数: 20

摘要

A large scale synthesis of the topical carbonic anhydrase inhibitors AL-4623A (13a⊙ HCl) and AL-4862 (13b) from 3-acetyl-2, 5-dichlorothiophene (“DCAT”, 1) is described. Reaction of 1 with NaSBn gave thioether 2, which was converted via sulfenyl chloride 3 and sulfenamide 5 to sulfonamide 6. Bromination of 6 gave bromo ketone 7, which upon reduction with (+)-B-chlorodiisopinocampheylborane and cyclization of the resulting ...