26164-26-1

Usage

Uses

1. Used in Organic Synthesis:
(S)-(+)-alpha-Methoxyphenylacetic acid is used as a reactant in organic synthesis for the production of different compounds.
2. Used in Pharmaceutical Industry:
(S)-(+)-alpha-Methoxyphenylacetic acid is used as a reactant for the synthesis of biologically active molecules, which have potential applications in the pharmaceutical industry. These molecules include:
a. Acyclonucleoside phosphonates: These are structural analogs of adefovir, an antiviral drug used to treat chronic hepatitis B infection.
b. Labeled discodermolide: (S)-(+)-alpha-Methoxyphenylacetic acid is used for studying binding to tubulin, which can provide insights into the development of new anti-cancer drugs.
c. 10-Isocyano-4-cadinene: This molecule is used for antifouling activity, which can be beneficial in the development of new materials and coatings to prevent biofouling.
d. Reactant in studies of immunostimulating chromanones gonytolides A-C: These compounds have potential applications in the development of new immunostimulating agents.
3. Used in Chemical Research:
(S)-(+)-alpha-Methoxyphenylacetic acid is also used as a reactant in various chemical reactions, such as:
a. Hydroxylations and epoxidations: These reactions are essential for the synthesis of various organic compounds and can provide valuable insights into the reactivity and selectivity of different functional groups.
b. Hydrogenations: This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and fine chemicals.

Purification Methods

Purify the acids by recrystallising from *C6H6/pet ether (b 80-100o). [Neilson & Peters J Chem Soc 1519 1962, Weizmann et al. J Am Chem Soc 70 1153 1948, Pirie & Smith J Chem Soc 338 1932, NMR: Dale & Mosher J Am Chem Soc 9 5 512 1973, for resolution: Roy & Deslongchamps Can J Chem 63 651 1985, Trost et al. J Am Chem Soc 1 0 8 4974 1986.] The racemic mixture has m 72o, b 121-122o/0.4mm, 165o/18mm (from pet ether) [Braun et al. Chem Ber 6 3 2847 1930]. [Beilstein 10 IV 566.]

InChI:InChI=1/C9H10O3/c1-12-8(9(10)11)7-5-3-2-4-6-7/h2-6,8H,1H3,(H,10,11)/p-1/t8-/m0/s1

Upstream product

• 7021-09-2 rac-methoxyphenylacetic acid 
• 17199-29-0 (S)-Mandelic acid 
• 77-78-1 dimethyl sulfate 
• 31528-01-5 (S)-2-Methoxy-2-phenylessigsaeure-4-nitrophenylester 
• 538-86-3 benzyl methyl ether 
• 124-38-9 carbon dioxide 
• 167476-45-1 1,1-bis(triethylsilyloxy)-2-methoxy-2-phenylethene 
• 66051-01-2 (S)-2-methoxy-2-phenylethanol 
• 114027-88-2 (S)-N-(α-Methylbenzyl)-(S)-2-methoxy-2-phenylacetamide 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 55137-68-3 (S)-(+)-O-methylmandeloyl chloride 
• 4870-65-9 2-bromophenylacetic acid 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 149-95-1 D-noradrenaline 
• 360557-72-8 (2S)-2-methoxy-2-phenylacetamide 
• 72565-52-7 (S)-Methoxy-phenyl-acetic acid (1S,2R)-1-ethyl-2-hydroxy-2-methyl-pent-3-ynyl ester 
• 72565-52-7 (S)-methoxy-phenyl-acetic acid (1R,2S)-1-ethyl-2-hydroxy-2-methyl-pent-3-ynyl ester 
• 135382-49-9 (S)-Methoxy-phenyl-acetic acid 2-oxo-2H-pyran-3-yl ester 
• 112893-81-9 (S)-Methoxy-phenyl-acetic acid (2S,6S)-2,6,10-trimethyl-undecyl ester 
• 114027-88-2 (S)-N-(α-Methylbenzyl)-(S)-2-methoxy-2-phenylacetamide 
• 112965-78-3 (S)-Methoxy-phenyl-acetic acid (2R,6R)-2,6,10-trimethyl-undecyl ester 
• 123643-00-5 (S)-O-Methylmandelic acid derivative of (2R,3R,4S,5R)-3-Hydroxy-2-methoxy-8-methyl-5-tetradecanoylnon-6-ene 1,4-lactone 
• 124126-42-7 (S)-2-((S)-2-Methoxy-2-phenyl-acetoxy)-3-propenylidene-decanoic acid methyl ester 
• 124126-42-7 (R)-2-((S)-2-Methoxy-2-phenyl-acetoxy)-3-propenylidene-decanoic acid methyl ester 
• 131832-04-7 (S)-Methoxy-phenyl-acetic acid (R)-2,2,2-trifluoro-1-o-tolyl-ethyl ester 
• 131832-04-7 (S)-Methoxy-phenyl-acetic acid (S)-2,2,2-trifluoro-1-o-tolyl-ethyl ester 
• 131832-03-6 (S)-Methoxy-phenyl-acetic acid (R)-2,2,2-trifluoro-1-(2,4,6-trimethyl-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Enantioselective carboxylation of α-methoxybenzyllithium generated via asymmetric lithiation with a t-BuLi/chiral bis(oxazoline) complex

Treatment of benzyl methyl ether with a t-BuLi/chiral bis(oxazoline) complex followed by carboxylation is shown to afford α-methoxy phenylacetic acid in high % ee (up to 95%). The asymmetric induction was proved to occur at the post-lithiation step.

The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes by using chiral salen catalyst

The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes was established. The reaction was successfully achieved by using (R,R)-SalenAlCl as the chiral catalyst and LiI as an additive at 0°C in dichloromethane. Moderate to good yields and up to 62% ee were obtained. The new system showed a good substrate scope in which both aromatic aldehydes and aliphatic aldehydes can be employed. The reaction provided the first catalytic and enantioselective approach to chiral β-iodo Baylis-Hillman ester adducts.

N-SUBSTITUTED ALPHA-AMINO AND ALPHA-HYDROXY CARBOXAMIDE DERIVATIVES

Disclosed are N-substituted α-amino and α-hydroxy carboxamides, pharmaceutical compositions comprising them, and methods of using them.

The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation

A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).

METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER

As shown by the following formula (1), after methyl laurate (2 mmol) and water (8 mL) are added to an ammonium pyrosulfate catalyst (5 mol%), a hydrolysis reaction of methyl laurate is carried out by heating for 24 hours at 60°C while stirring is performed, so that lauric acid can be obtained with a yield of 86%.

Effect of the concentration of organic modifier in an aqueous-ethanol mobile phase on the chromatographic retention and thermodynamic characteristics of the adsorption of enantiomers of α-phenylcarboxylic acids on silica gel with immobilized eremomycin antibiotic

Regularities of the chromatographic retention and thermodynamics of the adsorption of enantiomers of α-phenylcarboxylic acids on a chiral stationary phase with immobilized macrocyclic antibiotic eremomycin under conditions of reversed-phase liquid chromatography with aqueous-ethanol mobile phases are studied. Relationships between the retention characteristics of the acids, the enantioselectivity of their separation, and the concentration of organic modifier in the mobile phase are found. It is shown that the sterical structure of substituents on the chiral atoms of the acids affect the mechanism of retention. The compensation effect in the studied systems is considered.

N,N-diarylammonium pyrosulfate as a highly effective reverse micelle-type catalyst for hydrolysis of esters

Reverse micelle-type N,N-diarylammonium pyrosulfate (3-5 mol %) efficiently catalyzes the hydrolysis of esters (up to 100 mmol scale) under organic solvent-free conditions. The present method is successfully applied to the hydrolysis of various esters without the decomposition of the base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.

Enantioseparation of typical pesticides using cellulose carbamate stationary phases by capillary liquid chromatography

Cellulose-tris(3,5-dimethylphenylcarbamate) was initially synthesized as the chiral selector, then stable coated and bonded chiral stationary phases were prepared, respectively, using aminopropyl-functionalized silica gel as the support media. The prepared stationary phases were used for micro-column chiral separation by self-installed capillary high performance liquid chromatography system. Eighteen kind of chiral compounds including some typical pesticides were tested on both prepared chiral stationary phases and different chromatographic parameters such as resolution and retention time were comparatively investigated.

Kinetic resolution of (R,S)-pyrazolides containing substituents in the leaving pyrazole for increased lipase enantioselectivity

With hydrolysis of (R,S)-azolides in water-saturated methyl tert-butyl ether (MTBE) via Candida antarctica lipase B (CALB) as the model system, (R,S)-pyrazolides containing a leaving 3-, 4- or 3,4-substituted-pyrazole moiety are selected as the best substrates for preparing various optically pure carboxylic acids containing an α-chiral center. Great improvements of enzyme activity for the (R)-enantiomers with excellent enantioselectivity (VR/VS > 100) are obtainable, if (R,S)-pyrazolides containing a leaving 3- or 3,4-substituted-pyrazole moiety are employed for the hydrolysis or alcoholysis by methanol in anhydrous MTBE. A detailed kinetic analysis for (R,S)-N-2-phenylpropionylpyrazoles indicates that a bulky 3-substituent such as 3-(3-bromophenyl) or 3-(2-pyridyl) in the leaving pyrazole moiety has profound effects on decreasing the nucleophilic attack and proton transfer of catalytic serine for the slow-reacting enantiomer in anhydrous MTBE, as well as that and substrate affinity for both enantiomers in water-saturated MTBE. The resolution platform is also successfully applied to the hydrolysis of (R,S)-pyrazolides in water-saturated cyclohexane via Candida rugosa lipase (Lipase MY) having opposite enantioselectivity to CALB.

High-performance liquid chromatography separation of enantiomers of mandelic acid and its analogs on a chiral stationary phase

The enantiomers of mandelic acid and its analogs have been chromatographically separated on a chiral stationary phase (CSP) derived from 4-(3,5-dinitrobenzamido) tetrahydrophenanthrene. The rationale of separations of these compounds is discussed with respect to the method development for determining enantiomeric purity and possibility of obtaining enantiomerically pure materials by high-pressure liquid chromatography. The relationship of analyte structure to the extent of enantiomeric separation has been examined and separation factors (a) are presented for various groups of structurally related compounds. Chiral recognition models have been suggested to account for the observed separations. These models provide mechanistic insights into the chiral recognition process.