DIMETHYL 2-AMINOMALONATE, TECH

Base Information

• Chemical Name: DIMETHYL 2-AMINOMALONATE, TECH
• CAS No.: 53704-09-9
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.131
• Hs Code.: 2922499990
• Mol file: 53704-09-9.mol

Synonyms:Dimethyl 2-aminopropane-1,3-dioate;

Chemical Property of DIMETHYL 2-AMINOMALONATE, TECH

Chemical Property:

• Boiling Point: 155.7 °C at 760 mmHg
• PKA: 15.30±0.59(Predicted)
• Flash Point: 33.2 °C
• PSA: 78.62000
• Density: 1.205 g/cm³
• LogP: -0.64000
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Dimethyl 2-aminomalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Dimethyl 2-aminomalonate, tech (also known as dimethyl 2-aminopropane-1,3-dioate) serves as a key reagent in the synthesis of chiral 3-methoxy-2,5-morpholinediones, which act as versatile chiral cationic glycine equivalents. It reacts with chiral α-hydroxy acids to form dipeptolides, which are subsequently transformed via electrochemical methoxylation and lactonization into morpholinediones. These products are highly effective in amidoalkylation reactions, enabling the synthesis of non-proteinogenic α-amino acids with excellent enantioselectivity. The compound's utility lies in its role as a precursor for generating enantiomerically enriched amino acid derivatives, facilitating the production of both enantiomers from a single chiral source.

Technology Process of DIMETHYL 2-AMINOMALONATE, TECH

There total 4 articles about DIMETHYL 2-AMINOMALONATE, TECH 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%

dimethyl 2-(hydroxyimino)malonate (42937-74-6) → dimethyl 2-aminomalonate (53704-09-9)

Guidance literature:

With palladium on carbon; hydrogen; In methanol; at 20 ℃;

DOI:10.1016/j.tet.2011.05.112

Reference yield: 55.2%

dimethyl formamidomalonate (27160-23-2) → dimethyl 2-aminomalonate (53704-09-9)

Guidance literature:

With hydrogenchloride; In ethanol; Heating;

Reference yield:

malonic acid dimethyl ester (108-59-8) → dimethyl 2-aminomalonate (53704-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaNO₂; aq. acetic acid / 0 - 23 °C

2: 58.3 g / H₂ / Pd/C / ethanol / 12 h / 23 °C / 72400.7 Torr

With hydrogen; acetic acid; sodium nitrite; palladium on activated charcoal; In ethanol;

DOI:10.1021/ja035303i

upstream raw materials:

dimethyl 2-(hydroxyimino)malonate

dimethyl formamidomalonate

malonic acid dimethyl ester

Downstream raw materials:

[(N-benzyloxycarbonyl-glycyl)-amino]-malonic acid dimethyl ester

dimethyl diazomalonate

dimethyl N-benzyloxycarbonyl-L-prolylaminomalonate

2-{[1-Phenyl-meth-(E)-ylidene]-amino}-malonic acid dimethyl ester

Refernces

Electrogenerated chiral cationic glycine equivalents - Part 2: Chiral 3-methoxy-2,5-morpholinediones from (S)-α-hydroxy acids and dimethyl aminomalonate

10.1016/S0040-4020(98)00082-9

The research focuses on the synthesis and application of chiral 3-methoxy-2,5-morpholinediones, which are cyclic N,O-acetals, as excellent chiral cationic amino acid equivalents, particularly effective with larger nucleophiles. The purpose of the study was to develop a method for the synthesis of these compounds from dipeptolides formed between chiral cα-hydroxy acids and dimethyl aminomalonate, using a regioselective electrochemical methoxylation followed by intramolecular lactonization after decarboxylation. The researchers successfully synthesized the desired chiral 3-methoxy-2,5-morpholinediones and demonstrated their effectiveness in amidoalkylation reactions, with the ability to obtain both enantiomers of the new amino acid from a single chiral precursor. The chemicals used in the process included various chiral cα-hydroxy acids, dimethyl aminomalonate, acetyl chloride, thionyl chloride, sodium hydroxide, and nucleophiles such as allyl trimethyl silane and ally triphenyl silane. The study concluded that these chiral compounds are valuable due to their ease of separation from the starting chiral hydroxy acid by extraction and their potential use in the synthesis of non-proteinogenic co-amino acids.