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The use of these functional groups is exemplified in organic synthesis of the drug tolterodine, wherein one of the steps a phenol group is protected as its tosylate and the primary alcohol as its nosylate. The latter is a leaving group for displacement by diisopropylamine: [4] [nb 2] The tosyl group is also useful as a protecting group for amines.
A protecting group or protective group is introduced into a molecule by chemical modification ... Hideaki Muratake's 1990 synthesis using Tosyl protecting groups ...
The CH 3 C 6 H 4 SO 2 group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH. H 2 O. [6] As with other aryl sulfonic acids, TsOH is a strong organic acid. It is about one million times stronger than benzoic acid. [6]
Thus, tosylation followed by reduction allows for removal of a hydroxyl group. Likewise, TsCl is used to prepare sulfonamides from amines: [3] CH 3 C 6 H 4 SO 2 Cl + R 2 NH → CH 3 C 6 H 4 SO 2 NR 2 + HCl. The resulting sulfonamides are non-basic and, when derived from primary amines, are even acidic. TsCl reacts with hydrazine to give p ...
Tosyl groups can be removed from N-tosylamides almost instantaneously, using SmI 2 in conjunction with distilled water and an amine base. The reaction is even effective for deprotection of sensitive substrates such as aziridines: [11] Removal of a tosyl group from an N-tosylamide using SmI 2
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