26531-82-8

Basic information

• Product Name: Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetate
• Synonyms: Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetate;L-p-Hydroxyphenylglycine Methyl ester;Amino-(4-hydroxy-phenyl)-acetic acid methyl ester
• CAS NO: 26531-82-8
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.18854
• Mol File: 26531-82-8.mol

Chemical Properties

• Boiling Point: 303.17°C at 760 mmHg
• Flash Point: 137.152°C
• Appearance: /
• Density: 1.249g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.74±0.26(Predicted)
• CAS DataBase Reference: Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetate(26531-82-8)
• EPA Substance Registry System: Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetate(26531-82-8)

Safety Data

• Hazardous Substances Data: 26531-82-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetate is used as a key reagent for the synthesis of Amoxicillin, a widely prescribed antibiotic. Amoxicillin is effective in treating a range of bacterial infections, including respiratory, urinary, and skin infections. The compound's role in the production of Amoxicillin highlights its importance in the pharmaceutical industry, as it contributes to the development of life-saving medications.

InChI:InChI=1/C9H11NO3/c1-13-9(12)8(10)6-2-4-7(11)5-3-6/h2-5,8,11H,10H2,1H3/t8-/m0/s1

Upstream product

• 67-56-1 methanol 
• 32462-30-9 (S)-hydroxyphenylglycine 
• 4744-10-9 dimethoxypropane 
• 43189-12-4 (R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate 
• 6324-01-2 p-hydroxyphenylglycine 

Downstream Products

• 168158-40-5 L-2-amino-2-(4'-hydroxyphenyl)-N-methylacetamide 

Relevant articles and documents

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds having the general formula U1 - M - U2 wherein M is a linking group covalently joining R2, R3, R4 or R5 of U1 to an R2, R3, R4 or R5 group of U2; U1 and U2 have the general formula (I) and G, X1, X2, R2, R3, R3', R4, R4' and R5, are as described herein.

Using ionic liquid [EMIM][CH3COO] as an enzyme-'friendly' co-solvent for resolution of amino acids

An ionic liquid (IL), 1-ethyl-3-methylimidazolium acetate [EMIM][CH3COO], was used in 0-4.0 M (～60% IL, v/v), as a nonvolatile organic medium for the enzymatic resolution of amino acids. When dl-phenylalanine methyl ester was studied as a model substrate, high enantiomeric excesses (ee) of l-amino acid were obtained in all ionic concentrations; however, lower yields were observed at high IL concentrations. This IL is more enzyme-'friendly' than the hydrophilic organic solvent acetonitrile and those ILs containing chaotropic anions (such as [EMIM][OTs]). Among three proteases and two lipases investigated, lyophilized Bacillus licheniformis protease exhibited the best enantioselectivity and activity. Highly enantioselective resolutions were also produced for several other amino acids in 2.0 M IL. Interestingly, high ee were also found in deuterium oxide (D2O) rather than in ordinary water, and a further enhancement was achieved with the co-existence of [EMIM][CH3COO]. The heavy water effect was explained in terms of protein stabilization by D2O. The secondary structural changes of enzyme in various media were interpreted by the second derivatives of FT-IR spectra.

Ring-closing metathesis for the synthesis of side chain knotted pentapeptides inspired by vancomycin

A versatile method for the synthesis of bicyclic side chain knotted peptides inspired by vancomycin is described. The synthetic approach is based on the incorporation of a central amino acid derivative 3 having two allylic groups - introduced by a Stille

4-Amino cyclohexylglycine analogues as potent dipeptidyl peptidase IV inhibitors

Substituted 4-amino cyclohexylglycine analogues were evaluated for DP-IV inhibitory properties. Bis-sulfonamide 15e was an extremely potent 2.6 nM inhibitor of the enzyme with excellent selectivity over all counterscreens. 2,4-Difluorobenzenesulfonamide 1

The anandamide membrane transporter. Structurea€"activity relationships of anandamide and oleoylethanolamine analogs with phenyl rings in the polar head group region

A new series of arachidonic and oleic acids derivatives, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. A new series of anandamide and N-oleoylethanolamine analogs, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. Some of them efficaciously inhibit the uptake process with Ki values in the low micromolar range (2.4-21.2 μM). Strict structural requisites are needed to observe a significant inhibition and in no case inhibition of fatty acid amidohydrolase overlaps with inhibition of anandamide uptake.

FUSED INDOLES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to fused indole derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is in

D-Phenylglycine and D-4-hydroxyphenylglycine methyl esters via penicillin G acylase catalysed resolution in organic solvents

Penicillin G acylase in organic solvents catalyses specifically the acylation of the L-enantiomers of methyl esters of phenylglycine and 4- hydroxyphenylglycine. Hydrolytic reactions are prevented by controlling the water activity of the system and no excess of acylating agent is required. The process leads to the facile isolation of the enantiomerically pure D- enantiomer, which is of practical use for the preparation of β-lactam antibiotics. Electrospray mass spectroscopy has been applied to the study of the enantioselectivity of the enzyme. (C) 2000 Elsevier Science Ltd.

Synthesis of C-C biaryl segment of complestatin and chloropeptin: Approach to the right band CEF-ring system of complestatin

Studies toward C-C biaryl linkages between F-6 and E-3 of complestatin and F-7 and E-3 of chloropeptin involving Suzuki cross coupling reaction have been presented.

Synthesis of Isodityrosine, Dityrosine and Related Compounds by Phenolic Oxidation of Tyrosine and Phenylglycine Derivatives Using an Electrochemical Method

The phenolic oxidation of L-tyrosine derivatives by electrolysis and zinc reduction produced the coupling products leading to isodityrosine and dityrosine.The oxidation mode could be controlled by altering halogen substituents (Br or I) at two ortho positions of phenol groups.Additionally, this methodology was applied to 4-hydroxy-D-phenylglycine derivatives, providing the correspoinding oxidative products.