Camphorsulfonate

Camphorsulfonic acid

Camphorsulfonic acid

Chemical compound

Camphorsulfonic acid, sometimes abbreviated CSA or 10-CSA is an organosulfur compound. Like typical sulfonic acids, it is a relatively strong acid that is a colorless solid at room temperature and is soluble in water and a wide variety of organic substances.

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This compound is commercially available. It can be prepared by sulfonation of camphor with sulfuric acid and acetic anhydride:[1]

Although this reaction appears to be a sulfonation of an unactivated methyl group, the actual mechanism is believed to involve a retro-semipinacol rearrangement, deprotonation next to the tertiary carbocation to form an alkene, sulfonation of the alkene intermediate, and finally, semipinacol rearrangement to re-establish the ketone function.[2]

In organic synthesis, CSA and its derivatives can be used as resolving agents for chiral amines and other cations.[3][4] The synthesis of osanetant was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure devazepide.[5]

Camphorsulfonic acid is also being used for the synthesis of quinolines.[6] Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to as camsilate or camsylate, including trimetaphan camsilate and lanabecestat camsylate. Some studies (c.f. Lednicer) support that D-CSA was used for the resolution of Chloramphenicol.

References

  1. [1]
    Bartlett, Paul D.; Knox, L. H. (1965). "D,L-10-Camphorsulfonic acid (Reychler's Acid)". Organic Syntheses. 45: 12. doi:10.15227/orgsyn.045.0012.
  2. [2]
    Brückner, Reinhard (2002). Advanced organic chemistry : reaction mechanisms. San Diego: Harcourt/Academic Press. ISBN 9780080498805. OCLC 269472848.
  3. [3]
    Clark, Robin D.; Kern, John R.; Kurz, Lilia J.; Nelson, Janis T. (1990). "Preparation of Enatiomerically Pure Decahydro-6H-isoquino[2,1-g][1,6]naphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzo[a]quinolizinone Resolution". Heterocycles. 31 (2): 353. doi:10.3987/COM-89-5250 (inactive 2024-02-17).{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link)
  4. [4]
    Charette, André B. (2001). "3-Bromocamphor-8-sulfonic Acid". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rb283. ISBN 0471936235.
  5. [5]
    Reider, Paul J.; Davis, Paul; Hughes, David L.; Grabowski, Edward J. J. (1987). "Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonist". J. Org. Chem. 52 (5): 955–957. doi:10.1021/jo00381a052.
  6. [6]
    Chandra, Devesh; Dhiman, Ankit K; Kumar, Rakesh; Sharma, Upendra (2019). "Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reactiont". Eur. J. Org. Chem. 2019 (16): 2753–2758. doi:10.1002/ejoc.201900325. S2CID 107383202.
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