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

Base Information

• Chemical Name: α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide
• CAS No.: 120346-38-5
• Molecular Formula: C₁₃H₂₀N₂O₃
• Molecular Weight: 252.313
• Mol file: 120346-38-5.mol

Synonyms:

Chemical Property of α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide

There total 8 articles about α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide 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: 96.0%

(S)-2-amino-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid methyl ester (19728-71-3) + methylamine (74-89-5) → α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide (120346-38-5)

Guidance literature:

With sodium cyanide; In methanol; for 216h;

DOI:10.1002/adsc.201500056

Reference yield:

(3S,4R)-1-methyl-3-methyl-3-<(4S)-phenyloxazolidinyl>-4-(3,4-dimethoxyphenyl)azetidin-2-one (120346-36-3) → α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide (120346-38-5)

Guidance literature:

With lithium; tert-butyl alcohol; In tetrahydrofuran; ammonia; at -78 ℃; for 0.116667h;

DOI:10.1016/S0040-4020(01)86038-5

Reference yield:

N-(3,4-dimethoxybenzylidene)methanamine (17972-14-4) → α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide (120346-38-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine / 1.) CH₂Cl₂, -78 degC, 15 min.; 2.) CH₂Cl₂, allowed to warm to 0 degC (overnight)

2: 1.) lithium hexamethyldisilazide / 1.) THF, -78 degC, 1 h; 2.) -78 degC, overnight, warm to r.t.

3: Li, t-butanol / tetrahydrofuran; liquid ammonia / 0.12 h / -78 °C

With lithium; triethylamine; lithium hexamethyldisilazane; tert-butyl alcohol; In tetrahydrofuran; ammonia;

DOI:10.1016/S0040-4020(01)86038-5

upstream raw materials:

(3S,4R)-1-methyl-3-methyl-3-<(4S)-phenyloxazolidinyl>-4-(3,4-dimethoxyphenyl)azetidin-2-one

N-(3,4-dimethoxybenzylidene)methanamine

(3S,4R)-1-methyl-3-<(4S)-phenyloxazolidinyl>-4-(3,4-dimethoxyphenyl)azetidin-2-one

methyldopa

Refernces

• 1、 Ojima, Iwao,Chen, Hauh-Jyun C.,Qiu, Xiaogang. "NEW APPROACHES TO THE ASYMMETRIC SYNTHESIS OF NON-PROTEINOGENIC α-AMINO ACIDS AND DIPEPTIDES THROUGH CHIRAL β-LACTAM INTERMEDIATES". . p. 5307 - 5318. Retrieved 2007/10/02.