Mesylate
Encyclopedia
In chemistry
, a mesylate is any salt
or ester
of methanesulfonic acid
(C
H
3S
O
3H). 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
).
Mesylate esters are a group of organic compound
s 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 methanesulfonyl or CH3SO2- (Ms-) functional group. For example, methanesulfonyl chloride
is often referred to as mesyl chloride.
and methanesulfonyl chloride
in the presence of a base
, often amine
bases such as triethylamine
. 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.
Chemistry
Chemistry is the science of matter, especially its chemical reactions, but also its composition, structure and properties. Chemistry is concerned with atoms and their interactions with other atoms, and particularly with the properties of chemical bonds....
, a mesylate is any salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...
or ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
of methanesulfonic acid
Methanesulfonic acid
Methanesulfonic acid is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids. Salts and esters of methanesulfonic acid are known as mesylates. Methanesulfonic acid is used as an acid catalyst in organic reactions because it is non-volatile, strong acid...
(C
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
H
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
3S
Sulfur
Sulfur or sulphur is the chemical element with atomic number 16. In the periodic table it is represented by the symbol S. It is an abundant, multivalent non-metal. Under normal conditions, sulfur atoms form cyclic octatomic molecules with chemical formula S8. Elemental sulfur is a bright yellow...
O
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
3H). In salts, the mesylate is present as the CH3SO3− anion. When modifying the International Nonproprietary Name
International Nonproprietary Name
An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
of a pharmaceutical substance
Medication
A pharmaceutical drug, also referred to as medicine, medication or medicament, can be loosely defined as any chemical substance intended for use in the medical diagnosis, cure, treatment, or prevention of disease.- Classification :...
containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib
Imatinib
Imatinib is a drug used to treat certain types of cancer. It is currently marketed by Novartis as Gleevec or Glivec as its mesylate salt, imatinib mesilate . It is used in treating chronic myelogenous leukemia , gastrointestinal stromal tumors and some other diseases...
).
Mesylate esters are a group of organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
s that share a common functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
with the general structure CH3SO2O-R , abbreviated MsO-R, where R is an organic substituent. Mesylate is considered an excellent leaving group
Leaving group
In chemistry, a leaving group is a molecular fragment that departs with a pair of electrons in heterolytic bond cleavage. Leaving groups can be anions or neutral molecules. Common anionic leaving groups are halides such as Cl−, Br−, and I−, and sulfonate esters, such as para-toluenesulfonate...
in nucleophilic substitution
Nucleophilic substitution
In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms called the leaving group; the positive or partially positive...
reactions.
Mesyl is the term for the methanesulfonyl or CH3SO2- (Ms-) functional group. For example, methanesulfonyl chloride
Methanesulfonyl chloride
Methanesulfonyl chloride is a compound containing a sulfonyl chloride used to make methanesulfonates and to generate sulfene.-Preparation, manufacture and handling:Methanesulfonyl chloride is highly toxic, moisture sensitive, corrosive, and a lachrymator...
is often referred to as mesyl chloride.
Preparation
Mesylates may be prepared using an alcoholAlcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
and methanesulfonyl chloride
Methanesulfonyl chloride
Methanesulfonyl chloride is a compound containing a sulfonyl chloride used to make methanesulfonates and to generate sulfene.-Preparation, manufacture and handling:Methanesulfonyl chloride is highly toxic, moisture sensitive, corrosive, and a lachrymator...
in the presence of a base
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
, often amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
bases such as triethylamine
Triethylamine
Triethylamine is the chemical compound with the formula N3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine, for which TEA is also a common abbreviation....
. Mesylates can also be prepared by combining an alcohol, methanesulfonic anhydride
Methanesulfonic anhydride
Methanesulfonic anhydride is an is the acid anhydride of methanesulfonic acid. Like methanesulfonyl chloride, it may be used to generate mesylates ....
and base, although this method is generally used only if the nucleophilicity of chloride is a concern.