alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID

Base Information

• Chemical Name: alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID
• CAS No.: 77521-29-0
• Deprecated CAS: 126632-03-9,133481-32-0,139261-99-7,139559-02-7,74341-63-2,78729-80-3,85506-19-0,86495-63-8,83354-19-2,81323-87-7,92614-50-1,110592-37-5,79697-77-1
• Molecular Formula: C₇H₁₀N₂O₄
• Molecular Weight: 186.167
• Hs Code.: 2934999090
• UNII: J090588E6X
• DSSTox Substance ID: DTXSID20868301
• Nikkaji Number: J227.568F
• Wikipedia: AMPA
• Wikidata: Q66370552
• Pharos Ligand ID: 7242BWCTQ2BW
• Metabolomics Workbench ID: 67410
• ChEMBL ID: CHEMBL13378
• Mol file: 77521-29-0.mol

Synonyms:alpha Amino 3 hydroxy 5 methyl 4 isoxazolepropionic Acid;alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid;AMPA;AMPA, (+-)-Isomer;AMPA, (R)-Isomer;AMPA, (R)-Isomer, Monohydrobromide;AMPA, (S)-Isomer;AMPA, (S)-Isomer, Monohydrobromide

Chemical Property of alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID

Chemical Property:

• Appearance/Colour: White-to-Off White Powder
• Vapor Pressure: 5.3E-08mmHg at 25°C
• Melting Point: 240 °C
• Refractive Index: 1.541
• Boiling Point: 425.6 °C at 760 mmHg
• PKA: 2.15±0.10(Predicted)
• Flash Point: 211.2 °C
• PSA: 109.58000
• Density: 1.386 g/cm³
• LogP: 0.34330
• Storage Temp.: 2-8°C
• Solubility.: H2O: 1.2 mg/mL
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 186.06405680
• Heavy Atom Count: 13
• Complexity: 284

Purity/Quality:

99%+ ^*data from raw suppliers

(R,S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)NO1)CC(C(=O)O)N
• Recent ClinicalTrials: A Study of HB0030 Injection in Patients With Advanced Solid Tumors
• Recent NIPH Clinical Trials: Measurement of AMPA receptor density in persons with ARMS: a PET study
• Uses: A potent and selective agonist of the excitatory neurotransmitter L-glutamic Acid. AMPA does not interfere with binding sites for kainic acid in vitro, and AMPA- induced neuronal excitation is not significantly affected by NMDA antagonists AMPA is the defining agonist for the AMPA subgroup of ionotropic glutamate receptors, which mediate excitatory neurotransmission. Because AMPA does not interfere with binding sites for kainic acid or NMDA , it can be used to distinguish AMPA receptor-specific activity that contributes to a neuronal response. (R,S)-AMPA contains an equal mixture of the active (S)-enantiomer and the inactive (R)-enantiomer.

Technology Process of alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID

There total 6 articles about alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(bromomethyl)-2-(methoxymethyl)-5-methylisoxazol-3(2H)-one (153201-10-6) → (S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid (77521-29-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, -78 deg C, 3 h

2: TFA / CH₂Cl₂ / 15 h / Ambient temperature

3: aq. HCl, Dowex 50 WX₈-100 / 48 h / Heating

With hydrogenchloride; Dowex 50 WX₈-100; trifluoroacetic acid; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/S0957-4166(98)00275-4

Reference yield:

4-(bromomethyl)-2-(methoxymethyl)-5-methylisoxazol-3(2H)-one (153201-10-6) → (R)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid (77521-29-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA, 2.) NH₄Cl / 1.) THF, -78 deg C, 3 h, 2.) THF

2: TFA / CH₂Cl₂ / 15 h / Ambient temperature

3: aq. HCl, Dowex 50 WX₈-100 / 48 h / Heating

With hydrogenchloride; Dowex 50 WX₈-100; ammonium chloride; trifluoroacetic acid; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/S0957-4166(98)00275-4

Reference yield:

(2R,5R)-2-tert-Butyl-5-(2-methoxymethyl-5-methyl-3-oxo-2,3-dihydro-isoxazol-4-ylmethyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester (1026405-40-2) → (R)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid (77521-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 15 h / Ambient temperature

2: aq. HCl, Dowex 50 WX₈-100 / 48 h / Heating

With hydrogenchloride; Dowex 50 WX₈-100; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0957-4166(98)00275-4

upstream raw materials:

4-(bromomethyl)-2-(methoxymethyl)-5-methylisoxazol-3(2H)-one

(2R,5R)-2-tert-Butyl-5-(2-methoxymethyl-5-methyl-3-oxo-2,3-dihydro-isoxazol-4-ylmethyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester

Refernces