10290-61-6

Usage

Chemical Properties

White powder

InChI:InChI=1/C12H15NO3S/c1-17-8-7-10(12(15)16)13-11(14)9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3,(H,13,14)(H,15,16)

Upstream product

• 98-88-4 benzoyl chloride 
• 59-51-8 DL-methionine 
• 13602-48-7 3-benzoylamino-dihydro-furan-2-one 
• 5188-07-8 sodium thiomethoxide 
• 51127-20-9 4-(2-methylsulfanyl-ethyl)-2-phenyl-4H-oxazol-5-one 
• 4703-38-2 N-benzoylmethionine 
• 63-68-3 L-methionine 
• 7200-20-6 N-benzoyl-DL-methionine ethyl ester 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 65-85-0 benzoic acid 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 7732-18-5 water 
• 62-53-3 aniline 
• 58156-44-8 2,4,6-trinitrophenyl benzoate 

Downstream Products

• 348-67-4 D-methionine 
• 63-68-3 L-methionine 
• 4703-38-2 (R)-N-benzoylmethionine 
• 94067-89-7 N-benzoyl-L-methionine anilide 
• 7200-20-6 N-benzoyl-DL-methionine ethyl ester 
• 5468-52-0 N-benzoyl-2-aminobutyric acid 
• 59-51-8 DL-methionine 
• 55405-70-4 3-acetyl-2-ethylsulfanyl-2-[4-(2-methylsulfanyl-ethyl)-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl]-thiazolidine 
• 81577-91-5 N-<3-(methylthio)-propyl>benzamide 
• 92293-81-7 Benzoyl-DL-methionylglycin 
• 3054-52-2 N-benzoyl L-methionine sulphoxide 
• 1208867-91-7 C₃₃H₂₉NO₃S 
• 51127-20-9 4-(2-methylsulfanyl-ethyl)-2-phenyl-4H-oxazol-5-one 
• 1417544-50-3 N-{(S)-1-(benzo[d]oxazol-2-yl)-3-(methylthio)propyl}benzamide 

Relevant academic research and scientific papers

Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes

A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.

Asymmetric Aza-Diels-Alder Reactions of in Situ Generated β,β-Disubstituted α,β-Unsaturated N-H Ketimines Catalyzed by Chiral Phosphoric Acids

A novel asymmetric synthesis of dihydropyridinones with vicinal quaternary stereocenters has been realized by asymmetric aza-Diels-Alder reactions of 3-amido allylic alcohols with oxazolones enabled by chiral phosphoric acid catalysis. A series of aryl/alkyl- and alkyl/alkyl-disubstituted 3-amido allylic tertiary alcohols and 4-substituted oxazolones could be well tolerated in these reactions, producing dihydropyridinones with excellent diastereoselectivities and high enantioselectivities. Mechanistic study and control experiments were performed to shed light on the reaction mechanism, in which a configurationally defined β,β-disubstituted α,β-unsaturated N-H ketimine was proposed as the key intermediate.

Methionine derivative and application thereof

The invention relates to the technical field of chemical synthesis, and particularly discloses a methionine derivative and application thereof. The structure of the methionine derivative is shown as aformula (I). The methionine derivative provided by the invention is used as an oxidizing agent to be applied to an oxidation system, hydroxyl of a reaction substrate is oxidized into corresponding aldehyde or ketone, and no peculiar smell substance is generated in the reaction process; the yield of a target product is guaranteed, meanwhile, the reaction temperature can be effectively increased, the oxidation reaction can be normally conducted at the temperature higher than 0 DEG C, and the yield is high; and the methionine derivative can be recycled many times, the cost is saved, energy is saved, consumption is reduced, and the methionine derivative is environmentally friendly.

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

Palladium-catalyzed asymmetric decarboxylative allylation of azlactone enol carbonates: Fast access to enantioenriched α-allyl quaternary amino acids

We report a fast protocol for the synthesis of enantioenriched quaternary 4-allyl oxazol-5-ones. The key step is a Pd-catalyzed enantioselective Tsuji allylation of azlactone allyl enol carbonates, which can be easily prepared starting from racemic α-amino acids. The use of (R,R)-DACH-phenyl Trost chiral ligand allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. Scaling up the allylation protocol to gram quantities did not affect the yields end ee values. The produced 4-allyl azlactones can be converted into the corresponding quaternary amino acids or submitted to further synthetic elaborations exploiting the allyl moiety as a handle for the attachment of alkyl and aryl groups. After hydrolysis of the azlactone ring, the zwitterionic amino acids can be attained in enantiopure or nearly optically pure form through only one recrystallization step.

Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition

The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.

STRUCTURE AND SYNTHESIS OF HIGHLY FLUORINATED AMINO ACID DERIVATIVES

Methods of synthesizing polyfluorinated amino acid derivatives are disclosed, along with polyfluorinated amino acid derivatives produced from said methods, as well as compositions containing same. The synthesis methods utilize an oxazolone and a perfluoroarene to produce the polyfluorinated amino acid derivatives.

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.

Polyfluoroarylation of oxazolones: Access to non-natural fluorinated amino acids

Herein, conditions are provided for the formation and use of the oxazolone enolate for the nucleophilic substitution of highly fluorinated (hetero)arenes, which after unmasking yield highly fluorinated non-natural amino acids and derivatives. In addition, the properties and chemical behavior of this new class of amino acids are explored. The utility is demonstrated in the one pot synthesis of medicinally relevant 2-aminohydantoins.

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki–Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki–Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.