Microwave-assisted sulfamide synthesis

ORGN 618

Shahnaz Ghassemi, SGhassemi@biotage.com, Biotage, 1725 Discovery Drive, Charlottesville, VA 22911
The sulfamide compounds are noted for their broad and potent antibacterial activity. Currently, there are few sulfamides HIV-1 protease inhibitors used in chemotherapy for AIDS patients. The unsymmetric sulfamides appear to be more potent as protease inhibitors than the symmetric analogues due to the flipped conformation that occurs during binding. Unfortunately, most syntheses focus on symmetric sulfamides. The few methods available for unsymmetrical compounds rely on low-yielding synthetic steps that are neither general nor selective. This paper descries a general microwave assisted synthesis of unsymmetric sulfamide. Starting from a-amino acids and aldehydes or by the stepwise addition of CSI to tert-butanol followed by the addition of amines. Final products were rapidly isolated using automated flash purification system.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005