Melevodopa

Base Information

• Chemical Name: Melevodopa
• CAS No.: 7101-51-1
• Molecular Formula: C10H13 N O4
• Molecular Weight: 211.218
• Hs Code.: 2922509090
• UNII: M30686U4X4
• DSSTox Substance ID: DTXSID9048433
• Nikkaji Number: J33.787K
• Wikipedia: Melevodopa
• Wikidata: Q10967792
• NCI Thesaurus Code: C83927
• Metabolomics Workbench ID: 123316
• ChEMBL ID: CHEMBL1328898
• Mol file: 7101-51-1.mol

Synonyms:dl-dopa methyl ester;dopa methyl ester, (D)-isomer;L-dopa methyl ester;levodopa methyl ester;levodopa methyl ester hydrochloride;levodopa methyl ester hydrochloride, (DL)-isomer;melevodopa;methyl L-dopa

Chemical Property of Melevodopa

Chemical Property:

• Vapor Pressure: 1.86E-06mmHg at 25°C
• Refractive Index: 1.5150 (estimate)
• Boiling Point: 384.4°C at 760 mmHg
• Flash Point: 186.3°C
• PSA: 92.78000
• Density: 1.322g/cm³
• LogP: 0.84090
• Storage Temp.: 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 211.08445790
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

(S)-Methyl2-amino-3-(3,4-dihydroxyphenyl)propanoate 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(=C(C=C1)O)O)N
• Isomeric SMILES: COC(=O)[C@H](CC1=CC(=C(C=C1)O)O)N
• Description: CHF-1301 was launched as an injection in Italy for the treatment of patients with Parkinson's disease, particularly those with complications in their clinical responses. CHF-1301 is the methyl ester of L-Dopa (levodopa), the immediate precursor of dopamine. Thus, this prodrug is more soluble in water at physiological pH, better absorbed and slowly transformed into levodopa in vivo; it consequently improves the duration of action and prevents the rapid fluctuations in response or involontary movements (dyskinesia) observed during chronic treatment with levodopa. In patients with a delayed effect of levodopa (on-phenomenon) or a severe resistance to L-Dopa (off-phenomenon), CHF- 1301 significantly improves the onset and the stability of the'response.

Technology Process of Melevodopa

There total 16 articles about Melevodopa 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) + levodopa (59-92-7,90638-38-3) → L-DOPA methyl ester (7101-51-1)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.07.017

Reference yield: 99.0%

methanol (67-56-1) + dopa (63-84-3,90638-38-3) → (+/-)-3-(3,4-dihydroxyphenyl)-2-methyl-DL-alanine (7101-51-1,41439-83-2,71855-43-1)

Guidance literature:

With thionyl chloride;

DOI:10.1055/s-2008-1032164

Reference yield: 25.0%

L-Tyr-OMe (1080-06-4) → L-DOPA methyl ester (7101-51-1)

Guidance literature:

With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide; In acetonitrile; for 0.666667h; Irradiation;

DOI:10.1039/P19900003339

upstream raw materials:

methanol

dopa

L-Tyr-OMe

(+/-)-3-(3,4-dihydroxyphenyl)-2-methyl-DL-alanine

Downstream raw materials:

2-Amino-3-(3,4-dioxo-cyclohexa-1,5-dienyl)-propionic acid methyl ester

levodopa

(R)-(3,4-dihydroxyphenyl)alanine methyl ester

2-amino-3-(3,4-diacetoxyphenyl)-propionic acid

Refernces

• 1、 Brandhofer, Tobias,Derdau, Volker,García Manche?o, Olga,Méndez, María,P?verlein, Christoph,Stinglhamer, Martin. "Easy access to drug building-blocks through benzylic C-H functionalization of phenolic ethers by photoredox catalysis". supporting information. p. 6756 - 6759. Retrieved 2021/07/13.
• 2、 -. "Water-soluble L-DOPA esters". Paragraph 0082. . Retrieved 2018/05/24.