Esters methanesulfonates

Alkylsulphonate Esters. Methanesulfonate esters such as busulfan (7.72) produce clinical remission in chronic myelogenous leukaemia. Busulfan acts through an Sfj2 nucleophilic displacement and presumably crosslinks DNA, since the methanesulfonate... 

METHANESULFONIC ACID. ETHYL ESTER METHANESULFONIC ACID, METHYL ESTER... 

Tricaine methanesulfonate (MS-222). Tricaine methanesulfonate (3-aminobenzoic acid ethyl ester methanesulfonate MS-222) is widely used for the sedation and anesthetization of fish. The compound is 0.01% ionized at body pH and has a partition coefficient of 312. This relatively nonpolar lipophilic drug is rapidly absorbed from water and eliminated in freshwater and marine fish species. 

Synonyms 3-Aminobenzoic acid ethyl ester methanesulfonate ethyl-m-aminobenzoate methanesulfonate Trade names Finquel, Metacaine... 

NIR measurements on 100 live salmon were compared to postrigor measurements (42). The live salmon were anesthetized by placing the salmon in 12°C seawater with 0.02% w-amino-benzoic-acid-ethyl-ester-methanesulfonate. The salmons were measured both with a fiber-optic probe as described above and with a noncontact, diffuse reflectance fixed grating diode array spectrophotometer (DA 7000 Flexi-mode, Perten Instruments, Huddinge, Sweden). The diode array instrument scanned from 400 to 1700 nm in 5-nm steps. The salmon were measured at one spot as described above (53). The range of the salmon was 0.73-10.4 kg carcass weight and 8.2-23.2% fat. The cross-validated prediction error results were very similar for both instruments, namely, 1.4% (R = 0.90) fat for live salmon and 1.3-1.5% (R = 0.88-0.91) fat for postrigor salmon (Fig. 7.3.11). 

Optically pure (S) (+) 2 butanol was converted to its methanesulfonate ester according to the reaction shown... 

NaOH solution is added dropwise to an aqueous suspension of this ester at 40—70°C over 1 h and the reaction mixture kept for 2 h to give 86.6% DHNA of 98.7% purity (74), which is then esterified with (CgH O) to obtain PDNA. The esterification process is dramatically improved by adding a small amount of inorganic or organic acid, preferably methanesulfonic acid, benzene sulfonic acid, or naphthalene sulfonic acid subsequent isolation and crystallisation gives a pure product (75). 

In contrast to phosphorus esters, sulfur esters are usually cleaved at the carbon-oxygen bond with carbon-fluorine bond formation Cleavage of esteri nf methanesulfonic acid, p-toluenesidfonic acid, and especially trifluoromethane-sulfonic acid (tnflic acid) by fluoride ion is the most widely used method for the conversion of hydroxy compounds to fluoro derivatives Potassium fluoride, triethylamine trihydrofluoride, and tetrabutylammonium fluoride are common sources of the fluoride ion For the cleavage of a variety of alkyl mesylates and tosylates with potassium fluoride, polyethylene glycol 400 is a solvent of choice, the yields are limited by solvolysis of the leaving group by the solvent, but this phenomenon is controlled by bulky substituents, either in the sulfonic acid part or in the alcohol part of the ester [42] (equation 29)... 

British investigators (Haddow and Timmis 1951) synthesized and studied esters of the methanesulfonic acid. The most active derivative was the dimethylsulfonic ester of 1,4-butanedione, known as busulfan. Busulfan interacts with the thiol groups of proteins and amino acids some of its metabolites can alkylate the thiols of cysteine, peptides and proteins. Busulfan exerts selective cytotoxic activity in hematopoietic bone marrow cells and inhibits the formation of granulocytes and platelets. It slightly affects the lymphoid tissue. 

Malonic acid, amino-, diethyl ester, HYDROCHLORIDE, 40, 24 Malonic acid, bts(hydroxymethyl)-, DIETHYL ETHER, 40, 27 Malonitrile, condensation with tetra-cyanoethylene, 41, 99 2-Mercaptopyrimidine, 43, 6S hydrochloride of, 43, 68 Mercuric oxide in preparation of bromo-cyclopropane, 43, 9 Mesityl isocyanide, 41,103 5-Methallyl-l,2,3,4,5-pentachlorocyclo-pentadiene, 43, 92 Methane, dimesityl-, 43, 57 Methanesiileinyl chloride, 40, 62 Methanesulfonic acid, solvent for making peroxybenzoic acid from benzoic acid, 43, 93... 

C2oH fiClNO 149968-10-5) see Montelukast sodium [tx5-( )]-3-[2-(7-chloro-2-quinolinyl)ethenyl]-a-[2-[2-(l-methyl-l-[(tetrahydro-2//-pyran-2-yl)oxy]ethyl]phenyll-ethyl]benzenemethanol methanesulfonate (ester) (CjjHjgClNOjS 162489-71-6) see Montelukast sodium (5)-a-[3-[(E)-2-(7-chloro-2-quinolinyI)ethenyl]phenyl]-2-(l-hydroxy-l-methylethyl)benzenepropanol (C2i,H2xClN02) see Montelukast sodium (5)-a-[3-[( )-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(l-hydroxy-l-methylethyl)benzenepropanol methanesulfonate... 

Methanesulfonate esters of secondary alcohols also give Friedel-Crafts products in the presence of Sc(03SCF3)341 or Cu(03SCF3)2.42... 

In Entry 10, intramolecular acylation is followed by dehydrohalogenation. Entries 11 and 12 illustrate the use of polyphosphate ester. The cyclization in Entry 13 is done in neat methanesulfonic acid. 

Malonyl dichloride, 33, 20 2-Mercaptobenzimidazole, 30, 56 2-Mercaptobenzoxazole, 30, 57 Mercuric cyanide, 32, 31 Methallyl chloride, 32, 90 MeTHANEPHOSPHORIC ACID, DnSOPRO-PYL ESTER, 31, 33 Methanesulfonic acid, 30, 58 Methaneshlfonyl chloride, 30, 58 Methanol, 30, 31 32, 79 Methone, 31, 40... 

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