(2R)-2-azaniumyl-2-methylbutanedioate

Base Information

• Chemical Name: (2R)-2-azaniumyl-2-methylbutanedioate
• CAS No.: 14603-76-0
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.13
• DSSTox Substance ID: DTXSID40426366
• Wikidata: Q82239292
• Mol file: 14603-76-0.mol

Synonyms:(2R)-2-azaniumyl-2-methylbutanedioate;(2R)-2-ammonio-2-methylbutanedioate;DTXSID40426366;(2R)-2-azaniumyl-2-methyl-butanedioate;A808444

Chemical Property of (2R)-2-azaniumyl-2-methylbutanedioate

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 0.00395mmHg at 25°C
• Melting Point: 258 °C (decomp)
• Refractive Index: 1.524
• Boiling Point: 259.2 °C at 760 mmHg
• PKA: 2.32±0.28(Predicted)
• Flash Point: 110.6 °C
• PSA: 100.62000
• Density: 1.414 g/cm³
• LogP: -0.03660
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 146.04533274
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

α-Me-D-Asp-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)[O-])(C(=O)[O-])[NH3+]
• Isomeric SMILES: C[C@@](CC(=O)[O-])(C(=O)[O-])[NH3+]

Technology Process of (2R)-2-azaniumyl-2-methylbutanedioate

There total 14 articles about (2R)-2-azaniumyl-2-methylbutanedioate 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%

ethyl 2-((R)-2,2-dimethyl-4-methyl-3-(1-naphthoyl)-5-oxooxazolidin-4-yl)-acetate (1174715-60-6) → (R)-(-)-α-methylaspartic acid (14603-76-0)

Guidance literature:

With hydrogen bromide; In water; for 12h; Reflux; Inert atmosphere;

DOI:10.1021/ja9039604

Reference yield: 93.0%

(R)-N-(1-amino-3-methyl-2,5-dioxo-pyrrolidin-3-yl)-benzamide → (R)-(-)-α-methylaspartic acid (14603-76-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 80 ℃; for 6h;

DOI:10.1016/0040-4020(95)00665-U

Reference yield: 85.0%

(3R)-(-)-7-chloro-3-(ethoxycarbonyl)methyl-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one → (R)-(-)-α-methylaspartic acid (14603-76-0)

Guidance literature:

With hydrogenchloride; at 125 ℃; for 48h;

DOI:10.1021/ja0640142

upstream raw materials:

(R)-(+)-N-Acetyl-α-methyl-phenylalanin

ethyl methyl (S)-2-acetyl-2-methylsuccinate

(3R,5R)-(4-benzyl-3-methyl-2-oxo-5-phenylmorpholin-3-yl)acetic acid, methyl ester

ethyl 2-((R)-2,2-dimethyl-4-methyl-3-(1-naphthoyl)-5-oxooxazolidin-4-yl)-acetate

Refernces

• 1、 Carlier, Paul R.,Zhao, Hongwu,MacQuarrie-Hunter, Stephanie L.,DeGuzman, Joseph C.,Hsu, Danny C.. "Enantioselective synthesis of diversely substituted quaternary 1,4-benzodiazepin-2-ones and 1,4-benzodiazepine-2,5-diones". . p. 15215 - 15220. Retrieved 2007/10/03.
• 2、 Chinchilla, Rafael,Galindo, Nuria,Nájera, Carmen. "Chiral 3,6-dihydro-2H-1,4-oxazin-2-ones as alanine equivalents for the asymmetric synthesis of α-methyl α-amino acids (AMAAs) under mild reaction conditions". . p. 704 - 717. Retrieved 2007/10/03.