(2S)-2-amino-2,3-dimethylbutanoic acid

Base Information

• Chemical Name: (2S)-2-amino-2,3-dimethylbutanoic acid
• CAS No.: 53940-83-3
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.175
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID70428636
• Nikkaji Number: J656.281G
• Mol file: 53940-83-3.mol

Synonyms:53940-83-3;(2S)-2-amino-2,3-dimethylbutanoic acid;(S)-2-amino-2,3-dimethylbutanoic acid;D-Isovaline, 3-methyl-;(2S)-2-amino-2,3-dimethyl-butanoic acid;MFCD01318764;3-Methyl-L-isovaline;alpha-methylvaline;?-Methyl-L-valine;l-alpha-methyl-valine;alpha -Methyl-L-valine;2-METHYL-L-VALINE;H-(ME)VAL-OH;SCHEMBL62851;DTXSID70428636;GPYTYOMSQHBYTK-LURJTMIESA-N;AKOS015854212;(S)-2-amino-2,3-dimethylbutanoicacid;AB08744;AC-4453;CS-W013423;HY-W012707;DS-12691;D94633;O10056;(S)-2-AMINO-2,3-DIMETHYL-BUTYRIC ACID;A870607;(S)-(-)-alpha-Methylvaline, 99%, >=98.5% (TLC);alpha-Methyl-L-valine, 3-Methyl-L-isovaline (H-L-aMeVal-OH);916227-23-1

Chemical Property of (2S)-2-amino-2,3-dimethylbutanoic acid

Chemical Property:

• Vapor Pressure: 0.0499mmHg at 25°C
• Boiling Point: 217.7oC at 760 mmHg
• PKA: 2.40±0.14(Predicted)
• Flash Point: 85.5oC
• PSA: 63.32000
• Density: 1.038g/cm3
• LogP: 1.14470
• Storage Temp.: Store at RT.
• Solubility.: Water (Slightly)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 131.094628657
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

98% ^*data from raw suppliers

a-Methyl-L-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C)(C(=O)O)N
• Isomeric SMILES: CC(C)[C@@](C)(C(=O)O)N
• Uses: ALPHA-METHYL-L-VALINE HYDROCHLORIDE is used in the preparation of medicinal and herbicidal agents

Technology Process of (2S)-2-amino-2,3-dimethylbutanoic acid

There total 13 articles about (2S)-2-amino-2,3-dimethylbutanoic 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: 100.0%

(S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one (1007599-18-9) → (S)-α-Methylvaline (4378-19-2,26287-62-7,53940-82-2,53940-83-3)

Guidance literature:

With hydrogen bromide; In 1,4-dioxane; for 3h; Heating;

DOI:10.1021/ja801165z

Reference yield: 100.0%

(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one (1025364-74-2) → (S)-α-Methylvaline (4378-19-2,26287-62-7,53940-82-2,53940-83-3)

Guidance literature:

(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one; With hydrogen bromide; In water; Reflux; Inert atmosphere;

With Dowex-H⁺; Inert atmosphere;

DOI:10.1021/ja9039604

Reference yield: 87.4%

(S)-methyl 2-benzamido-2,3-dimethylbutanoate → (S)-α-Methylvaline (4378-19-2,26287-62-7,53940-82-2,53940-83-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 12h;

DOI:10.1002/hlca.19950780305

upstream raw materials:

DL-N-Trifluoroacetyl-α-methylvalin

2-amino-2,3-dimethylbutyramide

(2R,5S)-1-benzoyl-2-(tert-butyl)-5-isopropyl-3,5-dimethylimidazolidin-4-one

(2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on

Downstream raw materials:

(S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid

Boc-α-Me-Val-Gly-OEt

C₉H₁₃N₂O₂^(1-)*Na⁽¹⁺⁾

(2S)-2-isopropyl-2-methyl-1-((4-methyl-phenyl)sulfonyl)aziridine

Refernces

• 1、 Branca, Mathieu,Gori, Didier,Guillot, Regis,Alezra, Valerie,Kouklovsky, Cyrille. "Tertiary aromatic amide for memory of chirality: Access to enantioenriched α-substituted valine". . p. 5864 - 5865. Retrieved 2008/09/20.
• 2、 Kaptein, Bernard,Monaco, Vania,Broxterman, Quirinus B.,Schoemaker, Hans E.,Kamphuis, Johan. "Synthesis of dipeptides containing α-substituted amino acids; their use as chiral ligands in Lewis-acid-catalyzed reactions". . p. 231 - 238. Retrieved 2007/10/02.