Misplaced Pages

Mesylate

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from Mesylates) Salt or ester of methanesulfonic acid (CH₃–SO₂–OH)

Mesylate anion (structural formula)
Mesylate anion (ball-and-stick model)

In organosulfur chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH3SO3H). In salts, the mesylate is present as the CH3SO−3 anion. When modifying the international nonproprietary name of a pharmaceutical substance containing the group or anion, the spelling used is sometimes mesilate (as in imatinib mesilate, the mesylate salt of imatinib).

Mesylate esters are a group of organic compounds that share a common functional group with the general structure CH3SO2O−R, abbreviated MsO−R, where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions.

Preparation

Mesylate esters are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine.

Mesyl

Related to mesylate is the mesyl (Ms) or methanesulfonyl (CH3SO2) functional group. The shortened term itself was coined by Helferich et al. in 1938 similarly to tosyl adopted earlier. Methanesulfonyl chloride is often referred to as mesyl chloride.

Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to nitrogen, are resistant to hydrolysis. This functional group appears in a variety of medications, particularly cardiac (antiarrhythmic) drugs, as a sulfonamide moiety. Examples include sotalol, ibutilide, sematilide, dronedarone, dofetilide, E-4031, and bitopertin.

Natural occurrence

Ice core samples from a single spot in Antarctica were found to have tiny inclusions of magnesium methanesulfonate dodecahydrate. This natural phase is recognized as the mineral ernstburkeite. It is extremely rare.

See also

References

  1. International Nonproprietary Names Modified (PDF) (Report). World Health Organization. February 2006. INN Working Document 05.167/3. Retrieved 5 December 2008.
  2. Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 497. ISBN 978-0-471-72091-1.
  3. Rick L. Danheiser; Yeun-Min Tsai; David M. Fink (1966). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Organic Syntheses. doi:10.15227/orgsyn.066.0001. (a procedure illustrating the use of mesylates).
  4. Helferich, Burckhardt; Gnüchtel, Alfred (6 April 1938). "Ester der Methansulfonsäure in der Zuckergruppe". Berichte der deutschen chemischen Gesellschaft (A and B Series) (in German). 71 (4): 712–718. doi:10.1002/cber.19380710403. ISSN 0365-9488.
  5. Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis. doi:10.1002/047084289X.rm070.pub2
  6. Güner, Fatma Elif Genceli; Sakurai, Toshimitsu; Hondoh, Takeo (2013). "Ernstburkeite, Mg(CH3SO3)2·12H2O, a new mineral from Antarctica". European Journal of Mineralogy. 25 (1): 78–83. Bibcode:2013EJMin..25...78G. doi:10.1127/0935-1221/2013/0025-2257.
  7. Ernstburkeite, Mindat
Categories: