A short radiosynthesis of 6-[C3H3]-dorzolamide at very high specific activity and optical purity
✍ Scribed by W.-s. Eng; H. D. Burns; G. S. Ponticello; H. G. Selnick
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- French
- Weight
- 452 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
6-[C3H,]-Dorzolamide' was prepared starting from N,Nt-bis-Boc-6-desmethyldorzolamide. An efficient radiosynthesis was developed involving a regioselective and stereo-controlled 'H-methylation of the a-sulfone carbanion in the presence of the monoprotected sulfonamide anion. The methylation led to a mixture (ca. 7 : 1 for 4S,6R : 4S,6S) of the diastereomeric, tritiated products. Removal of the Boc protecting groups followed by HPLC purification of the resulting diastereomers afforded 6-[C3H,]-dorzolamide with > 99 % radiochemical purity, > 98.4 % enantiomeric excess, and a specific activity of > 74 CUmmol.