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A short radiosynthesis of 6-[C3H3]-dorzolamide at very high specific activity and optical purity
- Source :
- Journal of Labelled Compounds and Radiopharmaceuticals. 38:963-970
- Publication Year :
- 1996
- Publisher :
- Wiley, 1996.
-
Abstract
- 6-[C 3 H 3 ]-Dorzolamide£# was prepared starting from N,N'-bis-Boc-6-desmethyldorzolamide. An efficient radiosynthesis was developed involving a regioselective and stereo-controlled 3 H-methylation of the α-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-[C 3 H 3 ]-dorzolamide with > 99 % radiochemical purity, > 98.4 % enantiomeric excess, and a specific activity of > 74 Ci/mmol.
- Subjects :
- chemistry.chemical_classification
Bicyclic molecule
Chemistry
Organic Chemistry
Radiosynthesis
Diastereomer
Biochemistry
Chemical synthesis
Medicinal chemistry
Analytical Chemistry
Sulfone
Sulfonamide
chemistry.chemical_compound
Drug Discovery
Organic chemistry
Radiology, Nuclear Medicine and imaging
Enantiomeric excess
Spectroscopy
Carbanion
Subjects
Details
- ISSN :
- 03624803
- Volume :
- 38
- Database :
- OpenAIRE
- Journal :
- Journal of Labelled Compounds and Radiopharmaceuticals
- Accession number :
- edsair.doi...........c6cdffeffa53a6975e40a6ecb13f5882