methyl (2R)-2-amino-3-(4-hydroxyphenyl)propanoate

Base Information

• Chemical Name: methyl (2R)-2-amino-3-(4-hydroxyphenyl)propanoate
• CAS No.: 3410-66-0
• Molecular Formula: C10H13 N O3
• Molecular Weight: 195.218
• Hs Code.: 2922509090
• UNII: JLP688QYZ2
• DSSTox Substance ID: DTXSID50871823
• Nikkaji Number: J215.807H
• Mol file: 3410-66-0.mol

Synonyms:3410-66-0;D-tyrosine methyl ester;Methyl D-Tyrosinate;D-Tyrosine, methyl ester;D-Tyr-Ome;H-D-Tyr-OMe;methyl (2R)-2-amino-3-(4-hydroxyphenyl)propanoate;JLP688QYZ2;Tyrosine, methyl ester, D-;(R)-methyl 2-amino-3-(4-hydroxyphenyl)propanoate;UNII-JLP688QYZ2;SCHEMBL1255129;DTXSID50871823;MWZPENIJLUWBSY-SECBINFHSA-N;AKOS026745405;EN300-905354;(R)-2-amino-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Chemical Property of methyl (2R)-2-amino-3-(4-hydroxyphenyl)propanoate

Chemical Property:

• PSA: 72.55000
• LogP: 1.13530
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=C(C=C1)O)N
• Isomeric SMILES: COC(=O)[C@@H](CC1=CC=C(C=C1)O)N
• Uses: Methyl D-Tyrosinate is an intermediate in the synthesis of Oxybutynin Chloride (O868525), an inhibitor of proliferation and supresses gene expression in bladder smooth muscle cells.

Technology Process of methyl (2R)-2-amino-3-(4-hydroxyphenyl)propanoate

There total 14 articles about methyl (2R)-2-amino-3-(4-hydroxyphenyl)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: 100.0%

methanol (67-56-1) + ?Tyr (556-02-5,556-03-6,34537-57-0,55520-40-6,96946-98-4,60-18-4,18875-48-4,25619-78-7,30704-25-7) → tyrosine methyl ester (1080-06-4,3410-66-0,18869-47-1)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃; for 4.83333h;

Reference yield: 100.0%

methanol (67-56-1) + tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7) → D-tyrosine methyl ester (3410-66-0)

Guidance literature:

With thionyl chloride; Reflux;

DOI:10.1016/j.tetlet.2008.09.141

Reference yield: 86.0%

tyrosine methyl ester hydrochloride (3417-91-2,3728-20-9,68697-61-0) → tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7) + D-tyrosine methyl ester (3410-66-0) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7)

Guidance literature:

at 30 ℃; for 0.333333h; Yields of byproduct given; enzyme alcalase from Bacillus licheniforms; pH 8.0;

DOI:10.1039/c39860001514

upstream raw materials:

methanol

L-tyrosine

3-(4-Hydroxy-phenyl)-2-((E)-3-oxo-propenylamino)-propionic acid methyl ester

3-(4-Hydroxy-phenyl)-2-((E)-2-methyl-3-oxo-propenylamino)-propionic acid methyl ester

Downstream raw materials:

N-stearoyl-DL-tyrosine methyl ester

3-(4-Hydroxy-phenyl)-2-[2-(1H-indol-3-yl)-2-oxo-acetylamino]-propionic acid methyl ester

2-[(E)-2-(Diphenyl-phosphinoyl)-vinylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

2-[2-(5-Chloro-1H-indol-3-yl)-2-oxo-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester