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Usage

Uses

Used in Pharmaceutical Industry:
Alpha-Hydroxybenzenepropanoic acid methyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds for its unique reactivity and structural properties. It plays a crucial role in the development of new drugs and therapies.
1. As an intermediate in the synthesis of bortezomib analogs, which are 20S proteasome inhibitors. These inhibitors are essential in the treatment of multiple myeloma and other cancers by blocking the proteasome's ability to degrade proteins, leading to the accumulation of toxic proteins and cell death in cancer cells.
2. As a substrate in the amination of the benzylic C-H bonds. The aminated products are further used to prepare β-lactams, which are a class of antibiotics known for their broad-spectrum activity against various bacteria.
3. As an intermediate in one of the key synthetic steps for the preparation of YM-254890 analog, a selective Gαq/11 inhibitor. alpha-Hydroxybenzenepropanoic acid methyl ester has potential applications in treating various diseases, including cardiovascular and neurological disorders, by modulating the activity of specific signaling pathways in cells.

InChI:InChI=1/C10H12O3/c1-13-10(12)9(11)7-8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3/t9-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 20312-36-1 L-3-phenyllactic acid 
• 67-56-1 methanol 
• 54648-79-2 N,N’-diisopropyl-O-methylisourea 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 13674-16-3 methyl 2-hydroxy-3-phenylpropanoate 
• 185378-48-7 benzoic acid (1S)-1-methoxycarbonyl-2-phenylethyl ester 
• 108-05-4 vinyl acetate 
• 6362-58-9 methyl phenylpyruvate 
• 63-91-2 L-phenylalanine 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 828-01-3 phenyllactic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 70629-10-6 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-(S)-phenyllactic acid methyl ester 
• 54095-42-0 (S)-3-phenyllactic acid methyl ester o-nitrobenzenesulfonate 
• 121378-64-1 N-[(S)-2-Hydroxy-3-phenylpropanoyl]pyrrolidine 
• 188295-04-7 (2S)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide 
• 238421-32-4 methyl (2S)-2-(2-bromopropanoyloxy)-3-phenylpropanoate 
• 135912-77-5 (S)-2-methanesulfonyloxy-3-phenylpropionic acid methyl ester 
• 754989-19-0 methyl (2S)-2-methoxymethoxy-3-phenylpropanoate 
• 124706-56-5 (5S) 5-benzyl-4-hydroxy-3-methyl-2(5H)-furanone 
• 131066-60-9 methyl O-<<<(carbobenzoxyamino)methyl>methoxyphosphinyl>-L-leucyl>-(S)-2-hydroxy-3-phenylpropanoate 
• 1197031-90-5 (R)-(-)-Nα-methyl-Nβ-Boc-(D)-hydrazinophenylalanine methyl ester 

Relevant academic research and scientific papers

Phenylalanyl-tRNA synthetase of Escherichia coli K 10. Multiple enzyme-aminoacyl-tRNA complexes as a consequence of substrate specificity.

The interaction between Phe-tRNA(Phe) or other acyl-tRNA derivatives thereof and phenylalanyl-tRNA synthetase of Escherichia coli K 10 has been investigated by nonequilibrium dialysis, by fluorescence titration in the presence of 2-p-toluidinylnaphthalene-6-sulfonate, by the kinetics of the aminoacylation of tRNA(Phe), and by the kinetics of the catalytic hydrolysis of Phe-tRNA(Phe). Phe-tRNA(Phe), or derivatives thereof, forms two types of complexes with the synthetase. One type involves the attachment of the phenylalanyl moiety to the phenylalanine-specific site of the enzyme, and the other type, to the tRNA(Phe)-specific binding site. They resemble alternative modes of a destabilized enzyme-product complex and are predicted on the basis of thermodynamic considerations. The two modes of binding of acyl-tRNA compete with each other. The attachment of Phe-tRNA(Phe) to the phenylalanine-specific site dominates. At equilibrium, this complex is present at a fourfold higher concentration than the other type of complex. The HNO2 deaminated Phe-tRNA(Phe) binds exclusively to the site specific for L-phenylalanine. On the contrary, Ile-tRNA(Phe) adds at 94.1% to the tRNA(Phe)-specific site. The association of Phe-tRNA(Phe) with this site leads to enzymatic hydrolysis into L-phenylalanine and tRNA(Phe). The complex involving the phenylalanine-specific site is hydrolytically unproductive. L-Phenylalanine acts as an activator of the hydrolysis by occupying the amino acid specific site and by shifting the equilibrium between the complexes toward the binding ot Phe-tRNA(Phe) at the tRNA(Phe)-specific site. The association of Phe-tRNA(Phe) at the phenylalanine-specific site does not interfere sterically with the binding of free tRNA(Phe). The sequential addition of free and aminoacylated tRNA(Phe) exhibits negative cooperativity. Such a mechanism could help to expel the product from the enzyme.

ISOLATION OF β-PHENYLLACTIC ACID RELATED COMPOUNDS FROM PSEUDOMONAS SYRINGAE

Three metabolites, weakly phytotoxic on apple and bean leaves, have been isolated from Pseudomonas syringae pv papulans culture filtrates and their structures established by spectroscopic analysis.The trivial names of papuline, o-hydroxynitropapuline and papulinone were assigned to the three active substances.Papuline was the methylester of β-phenyllactic acid, and o-hydroxynitropapuline was its meta-hydroxy-para-nitro disubstituted derivative.Papulinone, a new β-lactone structurally related to β-phenyllactic acid, was identified as 4-(1-hydroxy-2-phenylethyl)-4-carbomethoxyoxyetan-2-one.

Trifluoromethanesulonic acid catalyzed alkylation of arenes with methyl (2R)-glycidate

Methyl (R)-glycidate (= methyl (R)-oxiranecarboxylate; 2) in superacidic trifluoromethanesulfonic acid medium reacts with electron-rich arenes to give α-hydroxy-β-arylpropanoate derivatives 3a-3f with high stereospecificity. At the same time, the observed

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters

A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

The enantioselective, catalytic vicinal difluorination of alkenes is reported by II/IIII catalysis using a novel, C2-symmetric resorcinol derivative. Catalyst turnover via in situ generation of an ArIIIIF2 species is enabled by Selectfluor oxidation and addition of an inexpensive HF–amine complex. The HF:amine ratio employed in this process provides a handle for regioselective orthogonality as a function of Br?nsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) is disclosed (>20:1 in both directions). Validation with electron deficient styrenes facilitates generation of chiral bioisosteres of the venerable CF3 unit that is pervasive in drug discovery (20 examples, up to 94:06 e.r.). An achiral variant of the reaction is also presented using p-TolI (up to >95 % yield).

Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen

A novel approach to synthesize enantiomerically pure α-hydroxy carboxylic derivatives is reported. A highly stereoselective oxidation of titanium(IV) enolates from chiral N -acyloxazolidinones is performed with oxygen under simple experimental conditions

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.

Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol

The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts.

Stereoselective synthesis of hantupeptins A, B and C common fragment

The stereoselective synthesis of the common fragment of Hantupeptine A, B and C is described using N-methylation of aminoacids, HATU mediated coupling reaction and diazotization of L-phenylalanine.