Methyl l-phenylalaninate

Base Information

• Chemical Name: Methyl l-phenylalaninate
• CAS No.: 2577-90-4
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• European Community (EC) Number: 219-934-7
• UNII: 10AT497I17
• Nikkaji Number: J31.465J
• Wikidata: Q27095740
• Metabolomics Workbench ID: 150027
• ChEMBL ID: CHEMBL51969
• Mol file: 2577-90-4.mol

Synonyms:(2S,3R)-(2-2H,3-2H)-phenylalanine methyl ester;L-phenylalanyl methyl ester;methyl phenylalanine;phenylalanine methyl ester;phenylalanine methyl ester, (D)-isomer;phenylalanine methyl ester, (DL)-isomer;phenylalanine methyl ester, hydrochloride, (D)-isomer;phenylalanine methyl ester, hydrochloride, (L)-isomer

Chemical Property of Methyl l-phenylalaninate

Chemical Property:

• Melting Point: 131-133 °C
• Boiling Point: 264.2 °C at 760 mmHg
• PKA: 7.13±0.33(Predicted)
• Flash Point: 126 °C
• PSA: 52.32000
• Density: 1.1 g/cm³
• LogP: 1.42970
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

97% ^*data from raw suppliers

(S)-Methyl 2-amino-3-phenylpropanoate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)N
• Isomeric SMILES: COC(=O)[C@H](CC1=CC=CC=C1)N

Technology Process of Methyl l-phenylalaninate

There total 111 articles about Methyl l-phenylalaninate 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: 100.0%

(E)-α-(N-acylamino)cinnamic acid methyl ester (64590-81-4) → methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4)

Guidance literature:

With hydrogen; (S)Fc-α-S(C5H5)Fe(C5H3(PPh2)CH(OH)C6H4(PPh2)); [Rh(norbornadiene)2]BF₄; In methanol; at 25 ℃; for 1h; under 750.075 Torr; Product distribution / selectivity;

Reference yield: 99.1%

→ methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester (33605-72-0)

Guidance literature:

Reference yield: 99.0%

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4)

Guidance literature:

With Amberlyst A₂₁; In dichloromethane; at 0 - 20 ℃; for 2h; stereoselective reaction;

DOI:10.1002/anie.202005109

upstream raw materials:

methanol

L-phenylalanine

H-Phe-OEt

N-Piperidinooxycarbonyl-L-phenylalanin-methylester

Downstream raw materials:

N-(S-benzyl-N-benzyloxycarbonyl-L-cysteinyl)-L-phenylalanine methyl ester

N-(α-oxo-isovaleryl)-L-phenylalanine methyl ester

N-(O-acetyl-N,N-phthaloyl-L-seryl)-L-phenylalanine-methyl ester

N-trifluoroacetyl-L-aspartyl-L-phenylalanine

Refernces

• 1、 Tekkam, Srinivas,Finn. "Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes". . p. 2833 - 2836. Retrieved 2017.
• 2、 Ungaro, Vitor A.,Liria, Cleber W.,Romagna, Carolina D.,Costa, Natália J. S.,Philippot, Karine,Rossi, Liane M.,Machini, M. Teresa. "A green route for the synthesis of a bitter-taste dipeptide combining biocatalysis, heterogeneous metal catalysis and magnetic nanoparticles". . p. 36449 - 36455. Retrieved 2015.
• 3、 Ichitsuka, Tomohiro,Komatsuzaki, Shingo,Masuda, Koichiro,Koumura, Nagatoshi,Sato, Kazuhiko,Kobayashi, Shū. "Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System". supporting information. p. 10844 - 10848. Retrieved 2021/05/31.
• 4、 Kervefors, Gabriella,Kersting, Leonard,Olofsson, Berit. "Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts". supporting information. p. 5790 - 5795. Retrieved 2021/03/08.