122674-93-5

Upstream product

• 67-56-1 methanol 
• 76466-16-5 2-(2-chlorophenoxy)propionic acid 
• 5445-17-0 Methyl 2-bromopropionate 
• 3046-25-1 o-chlorophenol, potassium salt 
• 95-57-8 2-monochlorophenol 
• 17392-83-5 (R)-Methyl lactate 
• 211184-89-3 2-(2-chloro-phenoxy)-propionyl chloride 
• 74411-15-7 2-(2-chlorophenoxy)propanoic acid methyl ester 

Downstream Products

• 76466-16-5 2-(2-chlorophenoxy)propionic acid 
• 25140-86-7 (R)-2-(2-chlorophenoxy) propanoic acid 
• 25140-86-7 (S)-2-(2-chlorophenoxy) propanoic acid 
• 140146-13-0 (R)-methyl 2-(2-chlorophenoxy) propionate 

Relevant academic research and scientific papers

A new method for production of chiral 2-aryloxypropanoic acids using effective kinetic resolution of racemic 2-aryloxycarboxylic acids

We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv2O) as an activating agent, bis(a-naphthyl)methanol ((α-Np)2CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.

Might the observed α2A-adrenoreceptor agonism or antagonism of allyphenyline analogues be ascribed to different molecular conformations?

We recently reported that the α2-adrenoreceptor (AR) ligand allyphenyline (9) significantly enhanced morphine analgesia (due to its α2C-AR agonism), was devoid of sedative side effects (due to its α2A-AR antagonism), preve

Optical resolution of aryloxypropionic acids and their esters by HPLC on cellulose tris-3,5-dimethyl-triphenylcarbamate derivative

Chiral chromatographic resolution of a series of antiphlogistic 2- aryloxypropionic acids and their methyl and ethyl esters was performed using a Chiralcel OD column. The CSP selected resolved most of the acids and esters efficiently, the enantiomers being well separated without requiring time consuming analysis. Chromatographic separation of R enriched samples was performed to determine the correct elution order. Using eluting systems such as hexane and 2-propanol, or hexane, 2-propanol and formic acid, the S enantiomer of all acids and esters was always found to elute first. We also considered the role of electron-donating or electron-withdrawing substituents (at the aryloxylic moiety) on the chiral resolution. It was shown that the electronic features of the substituents have more influence on the chiral interactions between the solutes and the CSP than their steric hindrance. Finally we determined, by molecular models, the interaction between CSP and solutes. In this way were able to determine all the potential sites for interactions, which are compatible with the conformations of the compounds and the structure of the stationary phase, and point out those interactions which enable chiral resolution.

Enantioselective inhibition: a strategy for improving the enantioselectivity of biocatalytic systems

Dextromethorphan (DM) and levomethorphan (LM) were found to be effective enantioselective inhibitors of Candida cylindracea lipase-catalyzed hydrolysis of a variety of (±)-arlypropionic and (±)-(arloxy)propionic esters. The enantioselectivity of the biocatalytic resolution of (±)-methyl 2-(2,4-dichlorophenoxy)propionate (DCPP) was enhanced 20-fold in the presence of either DM or LM. A general model for enantioselective inhibition has been developed, and a quantitative expression has been derived to show the underlying parameters that govern enantioselective inhibition. To define the mechanism of action of DM, a series of kinetic inhibition experiments was conducted with enantiomerically pure (R)-(+)-DCPP and (S)-(-)-DCPP. The observed inhibition pattern was that of partial noncompetitive inhibition for (R)-(+)-DCPP and that of pure noncompetitive inhibition for (S)-(-)-DCPP.

Enzyme catalysed hydrolysis of chlorophenoxypropionates

We report on the enzymatic hydrolysis of methyl 2-phenoxypropionate and of the following chlorinated derivatives: methyl o-chloro-, m-chloro-, p-chloro-, and o,p-dichloro-2-phenoxypropionates. α-Chymotripsyn, lipase, and pig liver esterase have an R enantioselectivity whereas subtilisin has an S enantioselectivity.Enantiomeric excess (e.e.) cover a wide range (from 5 to 100percent).