2-Amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid

Base Information

• Chemical Name: 2-Amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid
• CAS No.: 140158-50-5
• Molecular Formula: C₁₀H₁₆N₂O₄
• Molecular Weight: 228.248
• DSSTox Substance ID: DTXSID10930723
• Nikkaji Number: J468.922D
• Wikidata: Q12062353
• ChEMBL ID: CHEMBL113180
• Mol file: 140158-50-5.mol

Synonyms:2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid;2-amino-3-(hydroxy-5-tert-butylisoxazol-yl)propionic acid;alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionate;alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionate, (+-)-isomer;ATPA-tert

Chemical Property of 2-Amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid

Chemical Property:

• Vapor Pressure: 2.38E-07mmHg at 25°C
• Boiling Point: 406.8°Cat760mmHg
• PKA: 2.15±0.10(Predicted)
• Flash Point: 199.9°C
• PSA: 109.58000
• Density: 1.264g/cm³
• LogP: 1.33240
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: 10 mg/mL
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 228.11100700
• Heavy Atom Count: 16
• Complexity: 354

Purity/Quality:

98%Min ^*data from raw suppliers

ATPA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=C(C(=O)NO1)CC(C(=O)O)N

Technology Process of 2-Amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid

There total 13 articles about 2-Amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic 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: 77.0%

ethyl α-(ethoxycarbonyl)-α-(acetylamino)-3-methoxy-5-tert-butylisoxazole-4-propionate (95406-73-8) → (RS)-2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid (140158-50-5)

Guidance literature:

With hydrogen bromide; at 140 ℃; for 0.25h;

DOI:10.1021/jm50001a022

Reference yield: 30.0%

2-Acetylamino-2-(5-tert-butyl-2-methoxymethyl-3-oxo-2,3-dihydro-isoxazol-4-ylmethyl)-malonic acid dimethyl ester (192439-92-2) → (RS)-2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid (140158-50-5)

Guidance literature:

In trifluoroacetic acid; for 14h; Heating;

DOI:10.1016/S0223-5234(97)89085-X

Reference yield:

ethyl pivaloylacetate (17094-34-7) → (RS)-2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid (140158-50-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium ethoxide / 1.) ethanol, RT, 2 h, 2.) ethanol, 60 deg C, 3 h

2: 75 percent / aq. hydroxylammonium chloride, NaOH / 1.67 h / -5 °C

3: 24.2 percent / diethyl ether / 2 h

4: N-bromosuccinimide (NBS), benzoyl peroxide / CCl₄ / 1.33 h / Heating

5: ethanol / 5 h / Heating

6: 77 percent / 48percent aq. hydrobromic acid / 0.25 h / 140 °C

With sodium hydroxide; N-Bromosuccinimide; Perbenzoic acid; hydroxylamine hydrochloride; hydrogen bromide; sodium ethanolate; In tetrachloromethane; diethyl ether; ethanol;

DOI:10.1021/jm50001a022

upstream raw materials:

ethyl α-(ethoxycarbonyl)-α-(acetylamino)-3-methoxy-5-tert-butylisoxazole-4-propionate

2-Acetylamino-2-(5-tert-butyl-2-methoxymethyl-3-oxo-2,3-dihydro-isoxazol-4-ylmethyl)-malonic acid dimethyl ester

5-tert-butyl-3-methoxyisoxazole-4-carbaldehyde

5-tert-butyl-4-hydroxymethyl-3-methoxyisoxazole