An Efficient Preparation of Vinamidinium Hexafluorophosphate Salts

Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a − j in moderate to excellent recrystallized yields (28−90%). The cations are conveniently isolated as their hexafluorophosphate salts, which are easily handled nonhygroscopic soli...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-07, Vol.65 (15), p.4571-4574
Main Authors: Davies, Ian W, Marcoux, Jean-Francois, Wu, Jimmy, Palucki, Michael, Corley, Edward G, Robbins, Michael A, Tsou, Nancy, Ball, Richard G, Dormer, Peter, Larsen, Robert D, Reider, Paul J
Format: Article
Language:English
Subjects:
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Anti-Inflammatory Agents, Non-Steroidal - therapeutic use
Crystallography, X-Ray
Cyclooxygenase Inhibitors - chemical synthesis
Cyclooxygenase Inhibitors - chemistry
Cyclooxygenase Inhibitors - pharmacology
Cyclooxygenase Inhibitors - therapeutic use
Imides - chemical synthesis
Imides - chemistry
Imides - pharmacology
Imides - therapeutic use
Isomerism
Models, Molecular
Molecular Conformation
Nitrates - metabolism
Propylamines - chemical synthesis
Propylamines - chemistry
Propylamines - pharmacology
Propylamines - therapeutic use
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Summary:Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a − j in moderate to excellent recrystallized yields (28−90%). The cations are conveniently isolated as their hexafluorophosphate salts, which are easily handled nonhygroscopic solids. The nitro compound 3l is prepared in 91% yield by nitration of the parent vinamidinium 3k. The X-ray crystal structure is reported for the 2-phenyl isomer 3e and displays minimal overlap of the two π-systems.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000159u