Methyl 3-methoxy-L-tyrosinate

Base Information

• Chemical Name: Methyl 3-methoxy-L-tyrosinate
• CAS No.: 78148-37-5
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.244
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID20555946
• Nikkaji Number: J131.909D
• Wikidata: Q82437403
• Mol file: 78148-37-5.mol

Synonyms:78148-37-5;3-O-Methyl-L-DOPA Methyl Ester;Methyl 3-methoxy-L-tyrosinate;METHYL (2S)-2-AMINO-3-(4-HYDROXY-3-METHOXYPHENYL)PROPANOATE;(S)-2-AMINO-3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONIC ACID METHYL ESTER;3-Methoxy-L-tyrosine Methyl Ester;DTXSID20555946;AKOS015966024;N14845;EN300-1070268;(S)-2-AMINO-3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONICACIDMETHYLESTER

Chemical Property of Methyl 3-methoxy-L-tyrosinate

Chemical Property:

• Melting Point: >90°C (dec.)
• PSA: 81.78000
• LogP: 1.14390
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

3-O-Methyl-L-DOPA Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CC(C(=O)OC)N)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C[C@@H](C(=O)OC)N)O
• Uses: Protected 3-O-Methyl-L-DOPA (M303815). 3-O-Methyl-L-DOPA is the major metabolite of L-DOPA via catechol O-methyltransferase (COMT). 3-Methoxy-L-tyrosine is neither a substrate for nor an inhibitor of L-amino acid decarboxylase activity. Inhibition of COMT enhances the anti-Parkinson activity of L-DOPA.

Technology Process of Methyl 3-methoxy-L-tyrosinate

There total 7 articles about Methyl 3-methoxy-L-tyrosinate 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:

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride (32404-28-7) → (S)-2-Amino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid methyl ester (78148-37-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / SOCl₂ / Heating

2: 93 percent / aq. Na₂CO₃ / diethyl ether / 3 h / 25 °C

3: 60 percent / K₂CO₃; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C

4: mCPBA / CH₂Cl₂ / 40 °C

5: 453 mg / NH₃ / CH₂Cl₂; methanol / 1 h

6: 61 percent / K₂CO₃ / dimethylformamide / 6 h / 25 °C

7: H₂ / Pd/C / CH₂Cl₂

With thionyl chloride; ammonia; hydrogen; tetra-(n-butyl)ammonium iodide; sodium carbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Fischer esterification / 4: Baeyer-Villiger oxidation;

DOI:10.1021/jm050910x

Reference yield:

L-3-(3-methoxy-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester (881911-31-5) → (S)-2-Amino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid methyl ester (78148-37-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jm050910x

Reference yield:

(S)-3-(3-Acetoxy-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester → (S)-2-Amino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid methyl ester (78148-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 453 mg / NH₃ / CH₂Cl₂; methanol / 1 h

2: 61 percent / K₂CO₃ / dimethylformamide / 6 h / 25 °C

3: H₂ / Pd/C / CH₂Cl₂

With ammonia; hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050910x

upstream raw materials:

L-3-(3-methoxy-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester

N-[(phenylmethoxy)carbonyl]-3-hydroxy-O-(phenylmethyl)-L-tyrosine methyl ester

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride

Downstream raw materials:

N-<(3-hydroxy-4-methoxyphenyl)acetyl>-3-methoxy-D-tyrosine methyl ester

3-O-methyldopa

2-[2-(3-Benzyloxy-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid methyl ester

Refernces