2-Amino-3-(3,4-dimethoxyphenyl)propanoic acid

Base Information

• Chemical Name: 2-Amino-3-(3,4-dimethoxyphenyl)propanoic acid
• CAS No.: 55-59-4
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.244
• Hs Code.: 2922509090
• NSC Number: 121994
• UNII: OV6Z38VT4R
• DSSTox Substance ID: DTXSID901018930
• Wikidata: Q27285857
• Mol file: 55-59-4.mol

Synonyms:55-59-4;2-amino-3-(3,4-dimethoxyphenyl)propanoic acid;3,4-Dimethoxyphenylalanine;DL-3,4-Dimethoxyphenylalanine;3,4-Dimethoxyphenylalanine, DL-;3,4-Dimethoxy-dl-phenylalanine;UNII-OV6Z38VT4R;OV6Z38VT4R;Tyrosine, 3-methoxy-O-methyl-;MFCD00037201;NSC-121994;Tyrosine,3-methoxy-O-methyl-;NSC121994;S-3,4-DIMETHOXY-PHENYLALANINE;3,4-Dimethoxyphenylalanine #;SCHEMBL159000;2-AMINO-3-(3,4-DIMETHOXY-PHENYL)-PROPIONIC ACID;VWTFNYVAFGYEKI-UHFFFAOYSA-N;DTXSID901018930;2-Methyl-5-nitrobenzenesulfonicacid;AKOS000180195;AKOS022183305;AB01633;AB33629;DS-17334;SY044907;CS-0046967;FT-0613603;FT-0624392;FT-0631243;W16159;EN300-1844390;Q27285857;2-Amino-3-(3,4-dimethoxyphenyl)propanoic acid (H-DL-Phe(3,4-diOMe)-OH)

Chemical Property of 2-Amino-3-(3,4-dimethoxyphenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 254-257 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 374.3 °C at 760 mmHg
• PKA: 2.23±0.20(Predicted)
• Flash Point: 180.2 °C
• PSA: 81.78000
• Density: 1.214 g/cm³
• LogP: 1.35850
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

2-Amino-3-(3,4-dimethoxyphenyl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC(C(=O)O)N)OC
• Uses: 3-Methoxy-O-methyltyrosine is a starting material in the synthesis of peptide-based metal ion sensors.

Technology Process of 2-Amino-3-(3,4-dimethoxyphenyl)propanoic acid

There total 10 articles about 2-Amino-3-(3,4-dimethoxyphenyl)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:

(-)-2-amino-3-(3,4-dimethoxyphenyl)propionamide → 3-(3,4-dimethoxyphenyl)-2-aminopropionic acid (55-59-4)

Guidance literature:

With hydrogenchloride; water; for 20h; Reflux;

Reference yield:

3,4-dimethoxyphenylpyruvic acid (2460-33-5) → 3-(3,4-dimethoxyphenyl)-2-aminopropionic acid (55-59-4)

Guidance literature:

With pyridoxal 5'-phosphate; ethylenediaminetetraacetic acid; sodium diphenylglycine; In aq. buffer; at 50 ℃; pH=8;

DOI:10.1039/c6ra27525g

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → 3-(3,4-dimethoxyphenyl)-2-aminopropionic acid (55-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1: (i), (ii) aq. K₂CO₃, acetone, (iii) Na-Hg, H₂O

2: aq. HCl

With hydrogenchloride;

DOI:10.1139/v74-418

upstream raw materials:

N-benzoyl-3,4-dimethoxy-phenylalanine

chloroacetic acid

acetic anhydride

dimethyl sulfate

Downstream raw materials:

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

3-(3,4-dimethoxyphenyl)alanine ethyl ester

dopa

C₁₁H₁₄N₂O₆

Refernces

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

10.1021/acs.orglett.9b02819

The research explores an efficient method for synthesizing chiral heterocycles using a rhodium-catalyzed asymmetric ring opening reaction (ARO) of oxabicyclic alkenes. The study aims to address the challenges associated with using primary amines as nucleophiles in ARO reactions, which typically result in low yields and enantioselectivities. 2-nitrobenzenesulfonamide plays a crucial role as a pronucleophile in the rhodium-catalyzed asymmetric ring-opening reaction (ARO) of oxabicyclic alkenes. Specifically, it serves as a surrogate for primary amines, which traditionally face challenges such as low yields and enantioselectivities in ARO reactions. The 2-nitrobenzenesulfonamide derivatives of amino acids, such as alanine (2m), phenylalanine (2a), and valine (2o), are used to explore the ring-opening of oxabicyclic alkenes. These derivatives enable the formation of hydroxyesters and, subsequently, oxazinones through lactonization, demonstrating a high degree of enantioselectivity. The study concluded that the use of molecular sieves was crucial for driving the lactonization to completion, and the pairwise combination of chiral catalysts and nucleophiles allowed for the predictable and highly enantioselective synthesis of novel oxazinones and hydroxyesters.