2-(Methylamino)-3-phenylpropanoic acid

Base Information

• Chemical Name: 2-(Methylamino)-3-phenylpropanoic acid
• CAS No.: 2566-35-0
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• European Community (EC) Number: 849-766-5
• ChEMBL ID: CHEMBL135667
• DSSTox Substance ID: DTXSID801346562
• Nikkaji Number: J796.205C
• Mol file: 2566-35-0.mol

Synonyms:2-(methylamino)-3-phenylpropanoic acid;2566-35-0;N-Methyl-DL-phenylalanine HCl;N-Me-D-Phe-OH;methylphenylalanine;N-Me-Phe-OMe.HCl;N-methyl-d,l-phenylalanine;SCHEMBL38479;CHEMBL135667;DTXSID801346562;CAA56635;AKOS009941787;PB48203;PD196441;SY021348;CS-0197853;FT-0650103;FT-0693770;(2R)-2-(methylamino)-3-phenyl-propanoic acid;EN300-153838;Z446011606

Chemical Property of 2-(Methylamino)-3-phenylpropanoic acid

Chemical Property:

• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(CC1=CC=CC=C1)C(=O)O

Technology Process of 2-(Methylamino)-3-phenylpropanoic acid

There total 23 articles about 2-(Methylamino)-3-phenylpropanoic 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: 80.0%

2-oxo-3-(phenyl)propionic acid (156-06-9) + methylamine hydrochloride (593-51-1) → N-methylphenylalanine (2566-35-0)

Guidance literature:

With β-nicotinamide adenine dinucleotide 2’-phosphate reduced tetrasodium salt; D-glucose; delta-piperideine-2-carboxylate reductase from Pseudomonas putida; glucose dehydrogenase 901; In aq. buffer; at 25 ℃; for 24h; pH=8.5; Sealed tube; Enzymatic reaction;

DOI:10.1002/anie.201806893

Reference yield: 55.0%

2-bromo-3-phenylpropanoic acid (16503-53-0) + methylamine (74-89-5) → N-methylphenylalanine (2566-35-0)

Guidance literature:

In ethanol; at 0 - 20 ℃; for 48h;

DOI:10.1002/anie.201501275

Reference yield: 45.0%

(rac)-N-benzyl-N-methylphenylalanine (14464-19-8) → N-methylphenylalanine (2566-35-0)

Guidance literature:

With hydrogenchloride; 10% Pd/C; hydrogen; In water; acetic acid;

DOI:10.1002/ejoc.200701101

upstream raw materials:

α-(benzoyl-methyl-amino)-cinnamic acid

2-oxo-3-(phenyl)propionic acid

dimethyl amine

2-bromo-3-phenylpropanoic acid

Downstream raw materials:

L-FDAA-N-methyl-Phe

N-Methyl-L-phenylalanine

N-methyl-D-phenylalanine

N.N'-Dimethyl-2.4-bis--1.5-diphenyl-pentanon-(3)

Refernces

• 1、 Hyslop, Julia F.,Lovelock, Sarah L.,Sutton, Peter W.,Brown, Kristin K.,Watson, Allan J. B.,Roiban, Gheorghe-Doru. "Biocatalytic Synthesis of Chiral N-Functionalized Amino Acids". supporting information. p. 13821 - 13824. Retrieved 2018/09/27.
• 2、 Dzygiel, Pawel,Reeve, Toby B.,Piarulli, Umberto,Krupicka, Martin,Tvaroska, Igor,Gennari, Cesare. "Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies". supporting information; experimental part. p. 1253 - 1264. Retrieved 2009/04/07.