3-Amino-3-[3-(benzyloxy)phenyl]propanoic acid

Base Information

• Chemical Name: 3-Amino-3-[3-(benzyloxy)phenyl]propanoic acid
• CAS No.: 299439-16-0
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.316
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID70390526
• ChEMBL ID: CHEMBL1372044
• Mol file: 299439-16-0.mol

Synonyms:3-amino-3-[3-(benzyloxy)phenyl]propanoic acid;299439-16-0;3-amino-3-(3-phenylmethoxyphenyl)propanoic acid;3-Amino-3-(3-(benzyloxy)phenyl)propanoic acid;SMR000033622;MLS000047611;CHEMBL1372044;DTXSID70390526;HMS2291F18;MFCD02653340;STK501138;AKOS000266272;LS-02363;BB 0249691;CS-0270085;EU-0099952;3-Amino-3-(3-(benzyloxy)phenyl)propanoicacid;3-Amino-3-(3-benzyloxy-phenyl)-propionic acid;EN300-1287904;SR-01000095792;SR-01000095792-1

Chemical Property of 3-Amino-3-[3-(benzyloxy)phenyl]propanoic acid

Chemical Property:

• Melting Point: 224-225 °C (decomp)(Solv: ethanol (64-17-5); water (7732-18-5); acetone (67-64-1))
• Boiling Point: 455.8±45.0 °C(Predicted)
• PKA: 3.68±0.10(Predicted)
• PSA: 72.55000
• Density: 1.219±0.06 g/cm3(Predicted)
• LogP: 3.44040
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 271.12084340
• Heavy Atom Count: 20
• Complexity: 302

Purity/Quality:

98%Min ^*data from raw suppliers

3-Amino-3-[3-(benzyloxy)phenyl]propanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC=CC(=C2)C(CC(=O)O)N

Technology Process of 3-Amino-3-[3-(benzyloxy)phenyl]propanoic acid

There total 2 articles about 3-Amino-3-[3-(benzyloxy)phenyl]propanoic 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: 50.0%

malonic acid (141-82-2) + 3-Benzyloxybenzaldehyde (1700-37-4) → 3-amino-3-(3-(benzyloxy)phenyl)propanoic acid (299439-16-0)

Guidance literature:

With ammonium acetate; In ethanol; Reflux;

DOI:10.1039/c7md00058h

Reference yield: 41.0%

malonic acid (141-82-2) + 3-Benzyloxybenzaldehyde (1700-37-4) → 3-amino-3-(3-(benzyloxy)phenyl)propanoic acid (299439-16-0) + 3-<3-(phenylmethoxy)phenyl>-2-propenoic acid (122024-75-3,138835-16-2)

Guidance literature:

With ammonium acetate; In butan-1-ol; Heating;

DOI:10.1007/s11176-005-0377-9

Reference yield:

3-amino-3-(3-(benzyloxy)phenyl)propanoic acid (299439-16-0) + tert-butylisonitrile (119072-55-8,7188-38-7) + 6-chloro-3-formyl-1H-indole-2-carboxylic acid ethyl ester → 3-(1-(2-(3-(benzyloxy)phenyl)-4-oxoazetidin-1-yl)-2-(tert-butylamino)-2-oxoethyl)-6-chloro-1H-indole-2-carboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2,2-trifluoroethanol / 1.5 h / 130 °C / Microwave irradiation

2: lithium hydroxide; water / tetrahydrofuran / 20 °C

With water; lithium hydroxide; In tetrahydrofuran; 2,2,2-trifluoroethanol; 1: |Ugi Condensation;

DOI:10.1039/c7md00058h

upstream raw materials:

malonic acid

3-Benzyloxybenzaldehyde

Refernces

• 1、 Lebedev,Lebedeva,Sheludyakov,Kovaleva,Ustinova,Kozhevnikov. "Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium". . p. 1113 - 1124. Retrieved 2007/10/03.