2-Methoxy-L-Phenylalanine

Base Information

• Chemical Name: 2-Methoxy-L-Phenylalanine
• CAS No.: 193546-31-5
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• DSSTox Substance ID: DTXSID60444688
• Nikkaji Number: J848.232B
• Mol file: 193546-31-5.mol

Synonyms:2-Methoxy-L-Phenylalanine;193546-31-5;(S)-2-Amino-3-(2-methoxyphenyl)propanoic acid;H-Phe(2-OMe)-OH;(2S)-2-AMINO-3-(2-METHOXYPHENYL)PROPANOIC ACID;L-2-METHOXYPHENYLALANINE;o-Methoxyphenylalanin;Phenylalanine, 2-methoxy-;2-METHOXYPHENYLALANINE;SCHEMBL155235;DTXSID60444688;(S)-2-METHOXYPHENYLALANINE;MFCD01632036;AKOS012010905;BS-15763;CS-0208985;N10810;A880256;J-012530

Chemical Property of 2-Methoxy-L-Phenylalanine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 206 °C(Solv: water (7732-18-5))
• Refractive Index: 1.56
• Boiling Point: 337.233 °C at 760 mmHg
• PKA: 2.29±0.10(Predicted)
• Flash Point: 157.753 °C
• PSA: 72.55000
• Density: 1.209 g/cm³
• LogP: 1.34990
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-Amino-3-(2-methoxyphenyl)propanoicacid 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC=C1CC(C(=O)O)N
• Isomeric SMILES: COC1=CC=CC=C1C[C@@H](C(=O)O)N

Technology Process of 2-Methoxy-L-Phenylalanine

There total 10 articles about 2-Methoxy-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: 67.0%

(S)-2-methoxyphenylalanine-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone → (S)-2-amino-3-(2-methoxyphenyl)propanoic acid (193546-31-5)

Guidance literature:

With hydrogenchloride; In methanol; water; at 80 ℃; for 1h; enantioselective reaction;

DOI:10.1039/c3cc44717k

Reference yield:

o-Methoxybenzyl bromide (52289-93-7) → (S)-2-amino-3-(2-methoxyphenyl)propanoic acid (193546-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaOEt / 1.) EtOH, 2.) EtOH, 3 h

2: 94 percent / aq. NaOH / 6 h / Heating

3: 63 percent / Aspergillus acylase I, aq. KOH / 72 h / 40 °C

With potassium hydroxide; sodium hydroxide; Aspergillus acylase I; sodium ethanolate;

DOI:10.1002/jhet.5570340321

Reference yield:

(+/-)-2-methoxyphenylalanine (22976-68-7) → (2R)-2-amino-3-(2-methoxyphenyl)propanoic acid (170642-31-6) + (S)-2-amino-3-(2-methoxyphenyl)propanoic acid (193546-31-5)

Guidance literature:

With phenylalanine ammonia-lyase from Petroselinum crispum; In aq. buffer; at 30 ℃; for 168h; pH=8.5; Time; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

upstream raw materials:

(2-methoxyphenyl)methanol

o-Methoxybenzyl bromide

2-acetylamino-2-(2-methoxybenzyl)malonic acid diethyl ester

3-(2'-methoxyphenyl)propenoic acid

Downstream raw materials:

N-tert-butoxycarbonyl-L-2-methoxyphenylalanyl-L-2-methoxyphenylalanine methyl ester

N-tert-butoxycarbonyl-D-2-methoxyphenylalanyl-L-2-methoxyphenylalanine methyl ester

N-tert-butoxycarbonyl-L-2-methoxyphenylalanyl-D-2-methoxyphenylalanine methyl ester

(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-(2-methoxy-phenyl)-propionic acid methyl ester

Refernces

• 1、 Yu, Jinhai,Li, Jing,Cao, Shuangyan,Wu, Ting,Zeng, Shuiyun,Zhang, Hongjuan,Liu, Junzhong,Jiao, Qingcai. "Chemoenzymatic synthesis of L-3,4-dimethoxyphenyl-alanine and its analogues using aspartate aminotransferase as a key catalyst". . p. 28 - 32. Retrieved 2018/11/26.
• 2、 Noisier, Anais F. M.,Harris, Craig S.,Brimble, Margaret A.. "Novel preparation of chiral α-amino acids using the Mitsunobu-Tsunoda reaction". supporting information. p. 7744 - 7746. Retrieved 2013/09/02.