2-Amino-2-methylsuccinic acid

Base Information

• Chemical Name: 2-Amino-2-methylsuccinic acid
• CAS No.: 3227-17-6
• Deprecated CAS: 866-73-9
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.131
• Hs Code.: 2922499990
• NSC Number: 14963,153559
• UNII: 70W4HTK6W3
• Nikkaji Number: J347.993E
• Wikidata: Q27896228
• Mol file: 3227-17-6.mol

Synonyms:2-methylaspartic acid;2-methylaspartic acid, (DL-Asp)-isomer;2-methylaspartic acid, (L-Asp)-isomer;alpha-methyl-DL-aspartate

Chemical Property of 2-Amino-2-methylsuccinic acid

Chemical Property:

• Vapor Pressure: 0.00395mmHg at 25°C
• Refractive Index: 1.4210 (estimate)
• Boiling Point: 259.2°C at 760 mmHg
• PKA: 2.32±0.28(Predicted)
• Flash Point: 110.6°C
• PSA: 100.62000
• Density: 1.4285 (rough estimate)
• LogP: -0.03660
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 147.05315777
• Heavy Atom Count: 10
• Complexity: 167

Purity/Quality:

98%min ^*data from raw suppliers

α-Me-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)N

Technology Process of 2-Amino-2-methylsuccinic acid

There total 20 articles about 2-Amino-2-methylsuccinic acid 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: 95.0%

((2R,4S)-3-Benzyl-4-methyl-5-oxo-2-phenyl-oxazolidin-4-yl)-acetic acid ethyl ester → L-α-methylaspartic acid (3227-17-6)

Guidance literature:

In hydrogen bromide; for 3h; Heating;

DOI:10.1016/S0040-4039(00)96091-X

Reference yield: 94.6%

2-<(2R,4S)-3-Benzoyl-2-(tert-butyl)-1,4-dimethyl-5-oxoimidazolidin-4-yl>essigsaeure (103825-52-1) → L-α-methylaspartic acid (3227-17-6)

Guidance literature:

With hydrogen bromide; at 180 ℃; for 4h;

DOI:10.1002/hlca.19850680603

Reference yield: 91.0%

methyl 2-[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]acetate (1266681-10-0) → L-α-methylaspartic acid (3227-17-6)

Guidance literature:

methyl 2-[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-3-yl]acetate; With cesium hydroxide; water; at 70 ℃; for 3h;

With hydrogenchloride; In water;

DOI:10.1021/jo1022537

upstream raw materials:

(2S)-N-acetyl-3-(3',4'-diacetoxyphenyl)-2-methylalanine

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

2-<(2R,4S)-3-Benzoyl-2-(tert-butyl)-1,4-dimethyl-5-oxoimidazolidin-4-yl>essigsaeure

(2S,4S)-3-Benzoyl-2-isopropyl-6-methoxy-4-methyl-2,3,4,5-tetrahydro-pyrimidine-4-carboxylic acid methyl ester

Refernces

• 1、 Terashima,Achiwa,Yamada. "Studies on optically active amino acids. X. Studies on alpha-alkyl-alpha-amino acids. V. Absolute configuration of biochemically active (-)-alpha-methyl-3,4-dihydroxyphenylalanine.". . p. 579 - 582. Retrieved 1966.
• 2、 Najera, Carmen,Abellan, Tomas,Sansano, Jose M.. "Asymmetric synthesis of α-Methyl α-Amino Acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-Tetrahydro-2-Pyrazinone structure". . p. 2809 - 2820. Retrieved 2007/10/03.
• 3、 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.