1912-23-8

Usage

Uses

Used in Organic Chemistry:
(S)-(-)-2-Phenoxypropionic Acid is used as a building block for the synthesis of other compounds, playing a crucial role in the development of new chemical entities.
Used in Chemical Research:
This acid is employed as a research tool in various chemical studies, contributing to the understanding of chemical reactions and the properties of different molecules.

InChI:InChI=1/C9H10O3/c1-7(9(10)11)12-8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)/t7-/m0/s1

Upstream product

• 42412-84-0 ethyl 2-phenoxypropionate 
• 2065-24-9 methyl 2-phenoxypropanoate 
• 54656-96-1 (S)-1-(4-pyridyl)ethanol 
• 446878-78-0 2-Phenoxypropionsaeureanhydrid 
• 940-31-8 2-phenoxypropionic acid 
• 71-36-3 butan-1-ol 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 
• 108-95-2 phenol 
• 32644-15-8 (S)-2-bromopropanoic acid 
• 10009-70-8 R-(+)-2-bromopropionic acid 
• 1445-91-6 (S)-1-phenylethanol 
• 122-35-0 2-phenoxypropanoic acid chloride 
• 62784-66-1 bis(1-naphthyl)methanol 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 

Downstream Products

• 15165-67-0 S-dichloprop 
• 1168136-49-9 (S,S)-2-phenoxypropionic anhydride 
• 1391916-85-0 C₁₈H₁₈N₄O₂ 
• 1914-69-8 6β-((S)-2-phenoxy-propionylamino)-penicillanic acid 

Relevant academic research and scientific papers

Ligand-Free Copper-Catalyzed Ullmann-Type C?O Bond Formation in Non-Innocent Deep Eutectic Solvents under Aerobic Conditions

An efficient and novel protocol was developed for a Cu-catalyzed Ullmann-type aryl alkyl ether synthesis by reacting various (hetero)aryl halides (Cl, Br, I) with alcohols as active components of environmentally benign choline chloride-based eutectic mixtures. Under optimized conditions, the reaction proceeded under mild conditions (80 °C) in air, in the absence of additional ligands, with a catalyst [CuI or CuII species] loading up to 5 mol% and K2CO3 as the base, providing the desired aryloxy derivatives in up to 98 % yield. The potential application of the methodology was demonstrated in the valorization of cheap, easily available, and naturally occurring polyols (e. g., glycerol) for the synthesis of some pharmacologically active aryloxypropanediols (Guaiphenesin, Mephenesin, and Chlorphenesin) on a 2 g scale in 70–96 % yield. Catalyst, base, and deep eutectic solvent could easily and successfully be recycled up to seven times with an E-factor as low as 5.76.

HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases

The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.

Mutual Kinetic Resolution of Racemic 3,4-Dihydro-3-methyl-2H-[1,4]benzoxazines with Acyl Chlorides of Racemic O-Phenyllactic Acids and DFT Modelling of Transition States

The effect of the electronic nature of the para substituent on the aromatic ring of 2-aryloxypropionyl chlorides on the stereochemical outcome of the acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its 7,8-difluoro-containing analogue has been studied. The geometries of the diastereoisomeric transition states and the corresponding Gibbs free enthalpies of activation were determined through DFT calculations at the COSMO-CH2Cl2-B3LYP-D3-gCP/def2-TZVP (or def2-SVP)//B3LYP-D3-gCP/def2-SVP level of theory. It has been found that a low-cost quantum chemical calculation at a chosen level of theory describes well the quantitative dependence of the selectivity of acylation on the structures of the reagents. The obtained results indicate that aromatic interactions between the reagents play a significant role in the process of stereodifferentiation, ensuring high selectivity of the acylation of benzoxazines with 2-aryloxyacyl chlorides.

Resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate using lyophilized mycelium of Aspergillus oryzae WZ007

The mycelium of Aspergillus oryzae WZ007 was successfully developed to kinetic resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R, S)-EHPP) for production of (R)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R)-EHPP). The key biocatalytic process parameters (pH, temperature, rotation speed and substrate concentration) were optimized. Under the optimum conditions, the optical purity of (R)-EHPP was improved up to >99% when the conversion was above 49%. A. oryzae WZ007 whole-cell lipase exhibited high reaction capacity, enantioselectivity and good reusability. The tolerable substrate concentration was 0.5 mol/L, and dry mycelium of A. oryzae WZ007 maintains over 80% of its initial activity after eight repeating cycles. Therefore the enzymatic preparation of (R)-EHPP route was suitable for industrial application.

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.

Kinetic resolution of α-substituted alkanoic acids promoted by homobenzotetramisole

A new method for catalytic nonenzymatic kinetic resolution of α-substituted alkanoic acids has been developed, which relies on their activation with DCC followed by enantioselective alcoholysis of the intermediate symm-anhydrides in the presence of the amidine-based catalyst homobenzotetramisole (HBTM). Moderate to excellent selectivity factors (s=5-96) have been obtained in the case of several classes of substrates, namely, α-aryl-, α-aryloxy/alkoxy-, α-halo-, α-azido-, and α-phthalimido-alkanoic acids. Under similar conditions, α-(arylthio/alkylthio)-alkanoic acids undergo dynamic kinetic resolution providing corresponding esters in up to 92 % ee and up to 93 % yield. Copyright

Enantioselective hydrogenation of α-aryloxy and α-alkoxy α,β-unsaturated carboxylic acids catalyzed by chiral spiro iridium/phosphino-oxazoline complexes

The iridium-catalyzed highly enantioselective hydrogenation of α-aryloxy and α-alkoxy-substituted α,β-unsaturated carboxylic acids was developed. By using chiral spiro phosphino-oxazoline ligands, the hydrogenation proceeded smoothly to produce various α-aryloxy- and α-alkoxy-substituted carboxylic acids with extremely high enantioselectivities (ee up to 99.8%) and reactivities (TON up to 10 000) under mild conditions. The hydrogenation of R-benzyloxy-substituted α,β-unsaturated acids provided an efficient alternative for the synthesis of chiral R-hydroxy acids after an easy deprotection. A mechanism involving a catalytic cycle between IrI and IrIII was proposed on the basis of the coordination model of the unsaturated acids with the iridium metal center. The rationality of the catalytic cycle, with an olefin dihydride complex as the key intermediate, was supported by the deuterium-labeling studies. The X-ray diffraction analysis of the single crystal of catalyst revealed that the rigid and sterically hindered chiral environment created by the spiro phosphino-oxazoline ligands is the essential factor that permits the catalyst to obtain excellent chiral discrimination. A chiral induction model was suggested on the basis of the catalyst structure and the product configuration.

Homobenzotetramisole-catalyzed kinetic resolution of α-Aryl-, α-Aryloxy-, and α-Arylthioalkanoic acids

Effective kinetic resolutions of α-aryl-, αaryloxy-, and α-arylthioalkanoic acids have been achieved via in situ generation of their symmetrical anhydrides and enantioselective alcoholysis in the presence of homobenzotetramisole (HBTM) 3.

A great improvement of the enantioselectivity of lipase-catalyzed hydrolysis and esterification using co-solvents as an additive

Addition of co-solvents such as tetrahydrofuran resulted in a great improvement of the enantioselectivity of lipase-catalyzed hydrolysis of butyl 2-(4-substituted phenoxy)propanoates in an aqueous buffer solution. On the other hand, lipase lyophilized from an aqueous solution containing the co-solvents catalyzed highly enantioselective esterification of 2-(4-substituted phenoxy)propionic acids, 2-(4-isobutylphenyl)propionic acid (ibuprofen), and 2-(6-methoxy-2-naph-thyl)propionic acid (naproxen) in an organic solvent. An increase in the E value up to two orders of magnitude was observed for some substrates. The origin of the enantioselectivity enhancement caused by the co-solvent addition was mainly attributed to a significant deceleration in the initial reaction rate for the incorrectly binding enantiomer, as compared with that for the correctly binding enantiomer. From the results of FT-1R, CD, and ESR spectra, the co-solvent addition was also found to bring about a partial destruction of the tertiary structure of lipase.

Parallel kinetic resolution of 2-methoxy and 2-phenoxy-substituted carboxylic acids using a combination of quasi-enantiomeric oxazolidinones

2-Methoxy-2-phenyl acetic acid and 2-phenoxy-2-phenylpropionic acid were resolved by the parallel kinetic resolution of their corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of lithiated oxazolidinones.