Mesylate
In chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH3SO3H). In salts, the mesylate is present as the CH3SO3− anion. When modifying the International Nonproprietary Name of a pharmaceutical substance containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib).[1]
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 an excellent leaving group in nucleophilic substitution reactions.
Mesyl is the term for the methylsulfonyl or CH3SO2- (Ms-) functional group. For example, methanesulfonyl chloride is often referred to as mesyl chloride.
Preparation
Mesylates may be prepared using an alcohol and methanesulfonyl chloride in the presence of a base, often amine bases such as triethylamine.[2] Mesylates can also be prepared by combining an alcohol, methanesulfonic anhydride and base, although this method is generally used only if the nucleophilicity of chloride is a concern.
See also
References
- ^ World Health Organization (February 2006). "International Nonproprietary Names Modified" (PDF). INN Working Document 05.167/3. WHO.
{{cite journal}}: Cite journal requires|journal=(help) Retrieved December 5, 2008. - ^ Rick L. Danheiser, Yeun-Min Tsai, and David M. Fink (1993). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 471. (a procedure illustrating the use of mesylates)