alpha-Amino-3-carboxymethoxy-5-methyl-4-isoxazolepropionic acid

Base Information

• Chemical Name: alpha-Amino-3-carboxymethoxy-5-methyl-4-isoxazolepropionic acid
• CAS No.: 130146-18-8
• Molecular Formula: C₉H₁₂N₂O₆
• Molecular Weight: 244.204
• DSSTox Substance ID: DTXSID80926613
• Nikkaji Number: J360.653H
• ChEMBL ID: CHEMBL291274
• Mol file: 130146-18-8.mol

Synonyms:2-amino-3-(3-(carboxymethoxy)-5-methylisoxazol-4-yl)propionic acid;2-AMOA;alpha-amino-3-carboxymethoxy-5-methyl-4-isoxazolepropionic acid;OMOA

Chemical Property of alpha-Amino-3-carboxymethoxy-5-methyl-4-isoxazolepropionic acid

Chemical Property:

• Vapor Pressure: 6.5E-11mmHg at 25°C
• Melting Point: 230(dec.)
• Boiling Point: 502.4°C at 760 mmHg
• Flash Point: 257.6°C
• PSA: 299.45000
• Density: 1.481g/cm³
• LogP: 0.00930
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Hot Methanol, Water
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 244.06953611
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

(R,S)-2-Amino-3-[3-(carboxymethoxy)-5-methyl-isoxazol-4-yl]-propionicAcidSesquihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NO1)OCC(=O)O)CC(C(=O)O)N
• Uses: A selective inhibitor of [3H]-AMPA binding in rat brain membranes. AMOA shows little affinity for [3H]-kainate binding sites or other sites on the NMDA receptor-channel complex, as represented by binding of [3H]-CPP, [3H]-gly or [3H]-MK-801. AMOA

Technology Process of alpha-Amino-3-carboxymethoxy-5-methyl-4-isoxazolepropionic acid

There total 3 articles about alpha-Amino-3-carboxymethoxy-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: 40.0%

methyl 2-acetamido-2-(methoxycarbonyl)-3-<3-<(ethoxycarbonyl)methoxy>-5-methylisoxazol-4-yl>propionate (130146-22-4) → AMOA (131417-68-0,130146-18-8)

Guidance literature:

With hydrogenchloride; for 10h; Heating;

DOI:10.1021/jm00105a019

Reference yield:

2-Acetylamino-2-(3-methoxy-5-methyl-isoxazol-4-ylmethyl)-malonic acid dimethyl ester (130146-20-2) → AMOA (131417-68-0,130146-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / 33percent hydrogen bromide / acetic acid / 20 h / Ambient temperature

2: 1.) potassium carbonate / 1.) acetone, 50 deg C, 90 min, 2.) 50 deg C, 20 h

3: 40 percent / 2 M hydrochloric acid / 10 h / Heating

With hydrogenchloride; hydrogen bromide; potassium carbonate; In acetic acid;

DOI:10.1021/jm00105a019

Reference yield:

methyl 2-(acetylamino)-2-(methoxycarbonyl)-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionate (130146-21-3) → AMOA (131417-68-0,130146-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) potassium carbonate / 1.) acetone, 50 deg C, 90 min, 2.) 50 deg C, 20 h

2: 40 percent / 2 M hydrochloric acid / 10 h / Heating

With hydrogenchloride; potassium carbonate;

DOI:10.1021/jm00105a019

upstream raw materials:

methyl 2-acetamido-2-(methoxycarbonyl)-3-<3-<(ethoxycarbonyl)methoxy>-5-methylisoxazol-4-yl>propionate

methyl 2-(acetylamino)-2-(methoxycarbonyl)-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionate

2-Acetylamino-2-(3-methoxy-5-methyl-isoxazol-4-ylmethyl)-malonic acid dimethyl ester