Talk:Mesylate

Reference for abrev. MS

Can someone please add to this article some information regarding the fact that Mesyl is allegedly abreviated to MS (Please provide a reference so we can substantiate the fact as presented on the disambiguation page MS). Thank you. --CyclePat (talk) 21:49, 17 December 2008 (UTC)[reply]

Seems like such a trivial thing to need a reference for, but here it is: Greene's Protective Groups in Organic Synthesis, by Peter G. M. Wuts and Theodora W. Greene. ChemNerd (talk) 02:53, 18 December 2008 (UTC)[reply]

What edition, and page number. Is it this book (the 4th edition? Or is it this book (the 3rd ed.). Thank you! --CyclePat (talk) 07:41, 21 December 2008 (UTC)[reply]

unsourced content

If anybody wants to find sources for this and add it back, fine by me (note, i changed sections to subsections):

Preparation

Mesylates may be prepared using an alcohol and methanesulfonyl chloride in the presence of a base, often amine bases such as triethylamine.^[1] 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.

Drug Application

Mesyl group appears in a variety of medications, particularly cardiac (i.e. “antiarrhythmic”) but as sulfonamide moiety:

E.g. Sotalol vs (isoprenaline), ibutilide, sematilide (vs Procainamide), risotilide... Dronedarone, Dofetilide, E-4031, etc.

Also: H2 receptor antagonist: sufotidine vs Loxtidine.

Bitopertin is yet another example of a drug containing the "mesyl" function, whereas mesoridazine which contains only one oxygen and is a sulfoxide.

^ 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)

there you go. Jytdog (talk) 14:40, 17 February 2015 (UTC)[reply]

Hey Smokefoot I totally get it that you are an expert and can look at a compound and say what it is. To a certain extent I am OK with letting that kind of stuff go unsourced but the content you added back also says "Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to carbon or nitrogen are robust." This statement needs a source, yes? Jytdog (talk) 20:17, 17 February 2015 (UTC)[reply]

Oh, thanks again for taking the time. Interesting how these conversations go: here I am thinking you are worried about sources for the occurrence of mesyl groups in various drugs, but you're concerned about sourcing on the non-reactivity of mesyl-N and mesyl-C bonds, sort of an geeky point. That source might be challenging to locate, because chemists tend not to write about things that don't react. The same assertion is laid out in Methanesulfonyl chloride#Methanesulfonamides without a source. In any case, I just found a citation that should satisfy you and improve these articles! Cheers, --Smokefoot (talk) 23:40, 17 February 2015 (UTC)[reply]

Why are some drugs provided as mesylates

eg Lenvatinib. Is it because it somehow makes them better drugs, or is it an accident of how the drug was synthesised ? - Rod57 (talk) 15:47, 14 December 2016 (UTC)[reply]

[1] 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)

[1]