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-nicotinoyl-L-phenylalanin-amide

N-(N-trifluoroacetyl-L-seryl)-L-phenylalanine methyl ester

For-Val-Phe-OMe

Refernces

Markedly enhancing enzymatic enantioselectivity in organic solvents by forming substrate salts

10.1021/ja984283v

The research aims to enhance enzymatic enantioselectivity in organic solvents without covalent alterations to the enzyme or substrate. The innovative approach proposed involves forming substrate salts with bulky counterions to increase steric hindrances for the less reactive substrate enantiomer, thereby improving enantioselectivity. The study was conducted using various structurally diverse chiral compounds, which were converted to salts using numerous Br?nsted-Lowry acids or bases, and then subjected to enzymatic transesterifications or hydrolyses. The results demonstrated that enzymatic reactions of these salts were significantly more enantioselective than those of the free substrates. Key chemicals used in the process included phenylalanine methyl ester, tropic acid, 2-benzylsuccinic acid 1-monomethyl ester, and various amines and acids for salt formation, such as benzoic acid, chloroacetic acid, 3,4,5-trimethoxycinnamic acid, and quinuclidine. The study concluded that the strategy was effective in organic solvents but not in water, where salts dissociate, and pointed to novel synthetic opportunities in nonaqueous enzymatic catalysis.