3417-91-2

Basic information

• Product Name: Methyl L-tyrosinate hydrochloride
• Synonyms: (S)-Methyl 2-aMino-3-(4-hydroxyphenyl)propanoate hydrochloride;Methyl L-tyrosite hydrochloride;Methyl L-Tyrosinate Hydrochloride,99%e.e.;L-Methyltyrosinate hydrochloride for synthesis;TYROSINE-OME HCL;H-TYR-OME HCL;H-L-TYR-OME HCL;METHYL L-TYROSINATE HYDROCHLORIDE
• CAS NO: 3417-91-2
• Molecular Formula: C₁₀H₁₄NO₃*Cl
• Molecular Weight: 231.68
• EINECS: 222-313-3
• Product Categories: Amino Acids;AMINOACIDS DERIVATIVES;Amino Acid Derivatives;Tyrosine [Tyr, Y];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Peptide Synthesis;Tyrosine
• Mol File: 3417-91-2.mol

Chemical Properties

• Melting Point: 192 °C (dec.)(lit.)
• Boiling Point: 330 °C at 760 mmHg
• Flash Point: 153.4 °C
• Appearance: Crystalline
• Density: 1.21g/cm3
• Refractive Index: 13 ° (C=2, MeOH)
• Storage Temp.: Store at RT.
• Water Solubility: very faint turbidity in Water
• Sensitive: Hygroscopic
• BRN: 3917353
• CAS DataBase Reference: Methyl L-tyrosinate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl L-tyrosinate hydrochloride(3417-91-2)
• EPA Substance Registry System: Methyl L-tyrosinate hydrochloride(3417-91-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 3417-91-2(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

InChI:InChI=1/C10H13NO3.ClH/c1-14-10(13)9(11)6-7-2-4-8(12)5-3-7;/h2-5,9,12H,6,11H2,1H3;1H/t9-;/m0./s1

Upstream product

• 67-56-1 methanol 
• 60-18-4 L-tyrosine 
• 77-76-9 2,2-dimethoxy-propane 
• 3978-80-1 Boc-Tyr-OH 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 74-88-4 methyl iodide 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 
• 946-80-5 (benzyloxy)benzene 
• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 3417-91-2 tyrosine methyl ester hydrochloride 
• 556-02-5 ?Tyr 
• 16870-43-2 L-tyrosine hydrochloride 
• 142847-18-5 N-(tert-butoxycarbonyl)tyrosine 

Downstream Products

• 4985-46-0 L-Tyr-NH₂ 
• 101575-09-1 N-benzoyl-L-tyrosine methylamide 
• 3641-25-6 N-tert-Pentyloxycarbonyl-L-tyrosin 
• 15149-72-1 N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosine methyl ester 
• 19391-50-5 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-(4-hydroxyphenyl)propanoate 
• 18658-65-6 N-tret-butoxycarbonyl-L-leucinyl-L-tyrosine methyl ester 
• 3799-87-9 methyl (2,2,2-trifluoroacetyl)-L-tyrosinate 
• 20898-06-0 Cbz-L-Asn-L-Tyr-OMe 
• 52126-91-7 Z(OMe)-Lys(Z)-Tyr-OMe 
• 106861-80-7 Cbz-L-Met-L-Tyr-OH 
• 42222-23-1 N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-tyrosine methyl ester 
• 2487-07-2 (S)-2-((R)-2-Benzyloxycarbonylamino-3-benzylselanyl-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 32886-16-1 Dec-Cys(CH2CO2Me)-Tyr-OMe 
• 30782-90-2 N-decanoyl-L-tyrosine methyl ester 

Relevant articles and documents

SYHTHESIS OF 2- AND 3-FLUOROTYROSINE WITH DILUTE FLUORINE GAS

Differences in reactivity and selectivity of fluorine gas towards L-tyrosine and the O,N-diacetylated derivative of L-tyrosine methyl ester have been exploited for the synthesis of 2- and 3-fluorotyrosine.Both 2- and 3-fluorotyrosine were identified by 2H, 19F and 13C NMR spectroscopy and high resolution mass spectrometry.The short synthesis time and high reaction yields allow this procedure to be used for the incorporation of the short lived positron emitting radionuclide 18F into the aromatic ring of L-tyrosine.

Polystyrene or Magnetic Nanoparticles as Support in Enantioselective Organocatalysis? A Case Study in Friedel-Crafts Chemistry

Heterogenized versions of the second-generation MacMillan imidazolidin-4-one are described for the first time. This versatile organocatalyst has been supported on 1% DVB Merrifield resin and Fe3O4 magnetic nanoparticles through a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. The resulting catalytic materials have been successfully applied to the asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes. While both catalytic systems can be easily recovered and admit repeated recycling, the polystyrene-based catalyst shows higher stability and provides better stereoselectivities.

RETRACTED ARTICLE: Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrug of 5-aminosalicylic acid for colon-specific drug delivery in inflammatory bowel disease

Mutual azo prodrug of 5-aminosalicylic acid with l-tyrosine was synthesized by coupling l-tyrosine with salicylic acid, for targeted drug delivery to the inflamed gut tissue in inflammatory bowel disease. The structure was confirmed by elemental analysis, IR and NMR spectroscopy. In vitro kinetic studies in rat fecal matter showed 87.18% release of 5-aminosalicylic acid with a half-life of 140.28 min, following first order kinetics. Therapeutic efficacy of the carrier system and the mitigating effect of the azo conjugate were evaluated in trinitrobenzenesulfonic acid-induced experimental colitis model. Myeloperoxidase activity was determined by the method of Krawisz et?al. The synthesized prodrug was found to produce comparable mitigating effect as that of sulfasalazine on colitis in rats.

Enhancement of the Anti-Inflammatory Activity of NSAIDs by Their Conjugation with 3,4,5-Trimethoxybenzyl Alcohol

The synthesis of derivatives of three nonspecific COX-1 and COX-2 inhibitors, ibuprofen, ketoprofen, naproxen is presented. These acids were connected via an amide bond with an amino acid (L-proline, L-tyrosine, and beta-alanine) used as a linker. The amino acid carboxylic group was esterified with 3,4,5 trimethoxybenzyl alcohol. The activity of the novel derivatives was examined in vivo on carrageenan-induced inflammation, and in vitro, as cyclooxygenase and lipoxygenase inhibitors. It was found that the new compounds were more potent anti-inflammatory agents than the parent drugs. Thus, the ibuprofen (21) and ketoprofen (16) derivatives reduced rat paw edema by 67 and 91% (the reduction by the relevant NSAIDs was 36 and 47%, respectively). They inhibited COX-2 more than the starting drugs (21 by 67%, ibuprofen 46%, 19 by 94%, ketoprofen 49%). Docking of compounds on the active sites of COX-1 and COX-2 reflects their in vitro activity. Thus, 19 adopts an unfavorable orientation for COX-1 inhibition, but it binds effectively in the binding pocket of COX-2, in agreement with the absence of activity for COX-1 and the high inhibition of COX-2. In conclusion, the performed structural modifications result in the enhancement of the anti-inflammatory activity, compared with the parent NSAIDs.

(2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative as well as preparation method and application thereof

The invention discloses a (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative shown as a formula (I) or an optical isomer, a diastereomer and racemate mixture and pharmaceutically acceptable salt thereof as well as a preparation method and application of the (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative. It is shown by comparison of results of a positive control group and a model group on lymphedema prevention experiments that the compound disclosed in the invention shows obvious anti-edema activity.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Solvent-freeN-Boc deprotection byex situgeneration of hydrogen chloride gas

An efficient, scalable and sustainable method for the quantitative deprotection of thetert-butyl carbamate (N-Boc) protecting group is described, using down to near-stoichiometric amounts of hydrogen chloride gas in solvent-free conditions. We demonstrate theex situgeneration of hydrogen chloride gas from sodium chloride and sulfuric acid in a two-chamber reactor, introducing a straightforward method for controlled and stoichiometric release of HCl gas. The solvent-free conditions allow deprotection of a wide variety ofN-Boc derivatives to obtain the hydrochloride salts in quantitative yields. The procedure obviates the need for any work-up or purification steps providing an uncomplicated green alternative to standard methods. Due to the solvent-free, anhydrous conditions, this method shows high tolerance towards acid sensitive functional groups and furnishes expanded functional group orthogonality.

PROCESS FOR MAKING BIARYL-BRIDGED CYCLIC PEPTIDES

The invention provides a method of preparing a biaryl-bridged cyclic peptide compound of Formula (I), where R1, R2, R3, R4, R5, R8, R7, R8, R9, R10, R11, R12, n and m are as defined in the specification. The biaryl-bridged cyclic peptides of Formula (I) are used in the preparation of pharmaceutically active substances, such as, for example, arylomycin and arylomycin analogues.

Preparation method of L-tyrosine derivative

The invention discloses a preparation method of an L-tyrosine derivative. The L-tyrosine derivative is O-alkyl-N-[fluorenylmethoxycarbonyl]-L-tyrosine, L-tyrosine is used as a starting material, the O-alkyl-N-[fluorenylmethoxycarbonyl]-L-tyrosine is prepared through esterification, amidation, etherification/hydrolysis and amidation in sequence, the total yield of the target product can reach 61.5%, and the ee value can reach 99% or above. The preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, lower cost and the like, for example, separation of triphenylphosphine oxide is avoided through etherification reaction. The method has the advantages of simple process, short route, mild reaction conditions and the like, for example, etherification and hydrolysis adopt a one-pot method; and the whole technological process generates few three wastes, the product yield and purity are high, and the method is suitable for industrial production.

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.