L-2-Aminomethylphenylalanine

Base Information

• Chemical Name: L-2-Aminomethylphenylalanine
• CAS No.: 158149-99-6
• Molecular Formula: C10H14 N2 O2
• Molecular Weight: 194.233
• DSSTox Substance ID: DTXSID80376134
• Wikidata: Q82164948
• Mol file: 158149-99-6.mol

Synonyms:L-2-Aminomethylphenylalanine;158149-99-6;959580-92-8;(2S)-2-amino-3-[2-(aminomethyl)phenyl]propanoic acid;(S)-2-Amino-3-(2-(aminomethyl)phenyl)propanoic acid;starbld0017864;o-aminomethylphenylalanine;SCHEMBL1818794;2-(aminomethyl)-L-phenylalanine;DTXSID80376134;AKOS026670281;AS-84331

Chemical Property of L-2-Aminomethylphenylalanine

Chemical Property:

• Melting Point: 224-225 °C
• Boiling Point: 377.5±42.0 °C(Predicted)
• PKA: 0.92±0.10(Predicted)
• PSA: 89.34000
• Density: 1.234±0.06 g/cm3(Predicted)
• LogP: 1.50030
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.105527694
• Heavy Atom Count: 14
• Complexity: 197

Purity/Quality:

HPLC>98% ^*data from raw suppliers

L-2-Aminomethylphenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of L-2-Aminomethylphenylalanine

There total 6 articles about L-2-Aminomethylphenylalanine 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: 95.0%

(S)-2-Amino-2-aminomethyl-3-phenyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (158149-98-5) → (S)-α,β-diamino-α-benzyl-propionic acid (158149-99-6)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1016/0957-4166(94)80114-2

Reference yield: 85.0%

di(tert-butyl) 1-[(2R,5S)-1-benzoyl-5-benzyl-1,2,3,4,5,6-hexahydro-3-methyl-2-(1-methylethyl)-4-oxopyrimidin-5-yl]hydrazine-1,2-dicarboxylate → (S)-α,β-diamino-α-benzyl-propionic acid (158149-99-6)

Guidance literature:

di(tert-butyl) 1-[(2R,5S)-1-benzoyl-5-benzyl-1,2,3,4,5,6-hexahydro-3-methyl-2-(1-methylethyl)-4-oxopyrimidin-5-yl]hydrazine-1,2-dicarboxylate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

With hydrogen; nickel; In methanol; dichloromethane; at 20 ℃; for 24h; under 51754.1 Torr;

With hydrogenchloride; In water; at 90 ℃;

DOI:10.1002/hlca.200490073

Reference yield: 55.0%

1-acetyl-4-benzyl-2-phenyl-imidazoline-4-carboxylic acid tert-butyl ester → (S)-α,β-diamino-α-benzyl-propionic acid (158149-99-6)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 24h; Reflux;

DOI:10.1021/ol9013552

upstream raw materials:

(S)-2-Amino-2-aminomethyl-3-phenyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(2S)-(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-amino-2-cyano-3-phenylpropanoate

Refernces

• 1、 Castellanos, Elena,Reyes-Rangel, Gloria,Juaristi, Eusebio. "Diastereoselective Electrophilic Amination of Chiral 1-Benzoyl-2,3,5,6-tetrahydro-3-methyl-2-(1-methylethyl)pyrimidin-4(1H)-one for the Asymmetric Syntheses of α-Substituted α,β-Diaminopropanoic Acids)". . p. 1016 - 1024. Retrieved 2007/10/03.