N-(2-Aminoethyl)-L-phenylalanine

Base Information

• Chemical Name: N-(2-Aminoethyl)-L-phenylalanine
• CAS No.: 81225-90-3
• Molecular Formula: C11H16N2O2
• Molecular Weight: 208.26
• DSSTox Substance ID: DTXSID50541771
• Wikidata: Q82418204
• Mol file: 81225-90-3.mol

Synonyms:81225-90-3;N-(2-Aminoethyl)-L-phenylalanine;SCHEMBL5158344;DTXSID50541771;(S)-2-((2-Aminoethyl)amino)-3-phenylpropanoic acid

Chemical Property of N-(2-Aminoethyl)-L-phenylalanine

Chemical Property:

• XLogP3: -2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 208.121177757
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NCCN
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NCCN

Technology Process of N-(2-Aminoethyl)-L-phenylalanine

There total 1 articles about N-(2-Aminoethyl)-L-phenylalanine 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:

L-Phenylalanine benzyl ester (962-39-0) → (S)-2-(2-Amino-ethylamino)-3-phenyl-propionic acid (81225-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₃CN; CH₃COOH / methanol / 2 h / 20 °C

2: anisole; AlCl₃ / CH₂Cl₂; nitromethane / 0.25 h / 20 °C

With aluminium trichloride; sodium cyanoborohydride; acetic acid; methoxybenzene; In methanol; nitromethane; dichloromethane;

DOI:10.1002/chem.200305448

Reference yield:

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) + (S)-2-(2-Amino-ethylamino)-3-phenyl-propionic acid (81225-90-3) → Nα-[N2-(5-dimethylamino-1-naphthalenesulfonyl)aminoethyl]-L-phenylalanine (289491-94-7)

Guidance literature:

With lithium carbonate; In water; acetonitrile; at 0 ℃; for 4h;

DOI:10.1016/S0040-4039(00)00444-5

Reference yield:

(S)-2-(2-Amino-ethylamino)-3-phenyl-propionic acid (81225-90-3) → N1-propyl-Nα-[N2-(5-dimethylamino-1-naphthalenesulfonyl)aminoethyl]-L-phenylalaninamide

Guidance literature:

Multi-step reaction with 2 steps

1: aq. Li₂CO₃ / acetonitrile / 4 h / 0 °C

2: HBTU; DIEA / dimethylformamide / 3 h

With lithium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.200305448

upstream raw materials:

L-Phenylalanine benzyl ester

Downstream raw materials:

N^α-[N²-(5-dimethylamino-1-naphthalenesulfonyl)aminoethyl]-L-phenylalanine