251565-91-0Relevant academic research and scientific papers
Selective hydrolysis of methanesulfonate esters
Chan, Lai Chun,Cox, Brian G.,Sinclair, Rhona S.
, p. 213 - 217 (2013/01/03)
The pH dependence of the hydrolysis of 4-{2-[(methylsulfonyl)oxy]ethyI} phenyl methanesulfonate, 1, and two carboxylate esters, ethyl 2(S)-ethoxy-3-(4-hydroxyphenyl)propionate, 2 and (2S)-2-ethoxy-3-[4-(2-{4- [(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]propanoate, 3, has been studied with a view to the selective removal of any remaining 1, following coupling with 2 to generate 3 in water at 95 °C (Scheme 1). It is shown that reduction of pH from that of the reaction conditions (pH ≈ 10) to pH 7-8 has little effect on the hydrolysis of 1, which is dominated by the water rate over this pH range, but reduces the rate of hydrolysis of the carboxylate ester group by 3 orders of magnitude (pH 7). This very strong quantitative difference in the response of the two types of ester group to pH change allows complete removal of 1 at low pH without measurable loss to the product ester, 3. The conclusions should be generally applicable to the removal of potentially genotoxic alkyl esters of methane sulfonic acid in the presence of carboxylic esters and other base-sensitive groups.
NEW PROCESS
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Page/Page column 6, (2008/06/13)
A process for the preparation of a compound of formula (I); in which R represents H or an acid protecting group which comprises reacting a compound of formula (II); in which R is as previously defined with a compound of formula (III); wherein X is a suitable leaving group in the presence of a base and using water as a diluent.
Comminuted form of(s)-2-ethoxy -3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid
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, (2008/06/13)
The present invention relates to a reduced particle size form of the compound (S)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid, as shown in formula (I), or a pharmaceutically acceptable salt thereof or a solvate of either thereof. The invention also concerns methods of treating one or more conditions associated with Insulin Resistance Syndrome using the reduced particle size form of the compound, or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for use in one or more of said conditions. The invention further concerns pharmaceutical compositions containing the reduced particle size form of the compound, or a pharmaceutically acceptable salt thereof, or a solvate thereof, as an active ingredient, as well as processes for the manufacture of the reduced particle size form of the compound, or a pharmaceutically acceptable salt thereof.
3-aryl-2-hydroxypropionic acid derivative (I)
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, (2008/06/13)
A novel 3-aryl-2-hydroxypropionic acid derivative, a process and intermediate for its manufacture, pharmaceutical preparations containing it and the use of the compound in clinical conditions associated with insulin resistance.
