methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate

Base Information

• Chemical Name: methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate
• CAS No.: 18181-08-3
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.24
• UNII: 49ARC1V0F1
• DSSTox Substance ID: DTXSID90939476
• Nikkaji Number: J55.186D
• Wikidata: Q76001923
• Mol file: 18181-08-3.mol

Synonyms:18181-08-3;methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate;alpha-Methyldopa methyl ester;158190-23-9;BRN 2649505;alpha-Methyl-3,4-dihydroxy-L-phenylalanine methyl ester;49ARC1V0F1;L-3-(3,4-Dihydroxyphenyl)-2-methylalanine methyl ester;ALANINE, 3-(3,4-DIHYDROXYPHENYL)-2-METHYL-, METHYL ESTER, L-;L-Tyrosine, 3-hydroxy-alpha-methyl-, methyl ester;Methyl (S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate;alpha-Dopa methyl ester;starbld0004048;UNII-49ARC1V0F1;SCHEMBL1485976;.ALPHA.-METHYL-MELEVODOPA;DTXSID90939476;Methyl 3-hydroxy-alpha-methyltyrosinate;LS-16070;CARBIDOPA IMPURITY B [EP IMPURITY];EN300-1070266;3-HYDROXY-.ALPHA.-METHYL-METHYL TYROSINATE

Chemical Property of methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate

Chemical Property:

• Vapor Pressure: 1.53E-06mmHg at 25°C
• Melting Point: 165-166 °C
• Boiling Point: 386.9°C at 760 mmHg
• PKA: 9.82±0.10(Predicted)
• Flash Point: 187.8°C
• Density: 1.28g/cm³
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

99%, ^*data from raw suppliers

α-MethyldopaMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C=C1)O)O)(C(=O)OC)N
• Isomeric SMILES: C[C@](CC1=CC(=C(C=C1)O)O)(C(=O)OC)N
• Uses: α-Methyldopa Methyl Ester is an impurity in the synthesis of L-α-Methyl DOPA Methyl Ester Hydrochloride which is a Methyldopa angiotensin II analog.

Technology Process of methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate

There total 2 articles about methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate 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: 71.7%

methanol (67-56-1) + methyldopa (555-30-6,555-29-3,88620-56-8) → L-methyldopa methyl ester (18181-08-3,1259578-15-8)

Guidance literature:

With hydrogenchloride; at 30 - 40 ℃; for 48h; Temperature;

Reference yield:

→ (±)-3-(3.4-dihydroxyphenyl)-2-methyl-DL-alanine methyl ester (158190-23-9,18181-08-3,1259578-15-8)

Guidance literature:

3,4-Dihydroxy-α-methyl-phenylalanin, Me., HCl, Δ;

Reference yield:

L-methyldopa methyl ester (18181-08-3,1259578-15-8) → (S)-N-(tert-butoxycarbonyl)-3-hydroxy-α-methyltyrosine (62631-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,4-dioxane

2: pyrrolidine / dichloromethane

With pyrrolidine; In 1,4-dioxane; dichloromethane;

DOI:10.1002/adsc.201500056

upstream raw materials:

methanol

methyldopa

Downstream raw materials:

(S)-N-(tert-butoxycarbonyl)-3-hydroxy-α-methyltyrosine

N-Boc-α-methyl-β-3,4-dimethoxyphenyl-L-alanine methylester

α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide

Refernces

• 1、 Walaszek, Dominika J.,Rybicka-Jasińska, Katarzyna,Smoleń, Sabina,Karczewski, Maksymilian,Gryko, Dorota. "Mechanistic Insights into Enantioselective C-H Photooxygenation of Aldehydes via Enamine Catalysis". . p. 2061 - 2070. Retrieved 2015/06/23.