(2S)-2-azaniumyl-3-(4-methoxyphenyl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(4-methoxyphenyl)propanoate
• CAS No.: 6230-11-1
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 29225090
• Mol file: 6230-11-1.mol

Synonyms:(2S)-2-azaniumyl-3-(4-methoxyphenyl)propanoate;O-methyl-L-tyrosine zwitterion;CHEBI:193554;4-methoxy-L-phenylalanine zwitterion;(2S)-2-ammonio-3-(4-methoxyphenyl)propanoate

Chemical Property of (2S)-2-azaniumyl-3-(4-methoxyphenyl)propanoate

Chemical Property:

• Appearance/Colour: white to very slightly beige powder
• Vapor Pressure: 1.62E-05mmHg at 25°C
• Melting Point: 259-261 °C (dec.)(lit.)
• Refractive Index: 1.559
• Boiling Point: 350.6 °C at 760 mmHg
• PKA: 2.24±0.10(Predicted)
• Flash Point: 165.8 °C
• PSA: 72.55000
• Density: 1.209 g/cm³
• LogP: 1.34990
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly, Sonicated)
• Water Solubility.: Very soluble in water.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 182

Purity/Quality:

99% ^*data from raw suppliers

O-Methyl-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: COC1=CC=C(C=C1)C[C@@H](C(=O)[O-])[NH3+]
• Uses: A non-natural Phenylalanine (P319415) derivative. O-Methyl-L-tyrosine, is used as a fine chemical intermediate.

Technology Process of (2S)-2-azaniumyl-3-(4-methoxyphenyl)propanoate

There total 46 articles about (2S)-2-azaniumyl-3-(4-methoxyphenyl)propanoate 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: 88.0%

(2S,5S)-N-<(S)-N-bis(methylthio)methylene-O-methylthyrosyl>-2,5-bis(methoxymethoxymethyl)pyrrolidine (108437-95-2) → O-Methyltyrosine (6230-11-1)

Guidance literature:

With hydrogenchloride; for 4h; Heating;

DOI:10.1016/S0040-4039(00)84807-8

Reference yield: 87.0%

(S)-4-methoxyphenylalanine-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone → O-Methyltyrosine (6230-11-1)

Guidance literature:

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

DOI:10.1039/c3cc44717k

Reference yield: 70.0%

N,N-diallyl-L-tyr (79561-74-3) → O-Methyltyrosine (6230-11-1)

Guidance literature:

With Wilkinson's catalyst; In water; acetonitrile; for 2h; Heating;

DOI:10.1016/S0040-4039(01)90356-9

upstream raw materials:

N-formyl-O-methyl-L-tyrosine

p-Methoxybenzyl bromide

trans-(2S,5S)-N--2,5-bis(methoxymethoxymethyl)pyrrolidine

L-tyrosine

Downstream raw materials:

O-methyl-L-tyrosine methyl ester hydrochloride

2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxyphenyl)-propionic acid

(S)-5-(4-methoxy-benzyl)-imidazolidine-2,4-dione

3-iodo-4-O-methyl-L-tyrosine

Refernces

• 1、 Liu, Jing,Wang, Bo,Li, Hongzhi,Xie, Yunchang,Li, Qinglian,Qin, Xiangjing,Zhang, Xing,Ju, Jianhua. "Biosynthesis of the anti-infective marformycins featuring pre-nrps assembly line N -formylation and O -methylation and post-assembly line C -hydroxylation chemistries". . p. 1509 - 1512. Retrieved 2015.
• 2、 -. "C(sp3) -C(sp2) Method for constructing key and β - aryl amino acid preparation method". Paragraph 0037; 0043-0044; 0046. . Retrieved 2021/10/27.
• 3、 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.