(R)-N-Benzylglutamic acid

Base Information

• Chemical Name: (R)-N-Benzylglutamic acid
• CAS No.: 73914-82-6
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.255
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID70703652
• Wikidata: Q82635857
• Mol file: 73914-82-6.mol

Synonyms:(R)-N-BENZYLGLUTAMIC ACID;73914-82-6;(2R)-2-(benzylamino)pentanedioic acid;(R)-2-(Benzylamino)pentanedioic acid;N-Benzyl-D-glutamic acid;SCHEMBL3387298;DTXSID70703652;MFCD00797916;(R)-N-BenZylglutamic acid (BZl-D-Glu-OH)

Chemical Property of (R)-N-Benzylglutamic acid

Chemical Property:

• PSA: 86.63000
• LogP: 1.48510
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

99%min ^*data from raw suppliers

(R)-N-BENZYLGLUTAMIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(CCC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)CN[C@H](CCC(=O)O)C(=O)O

Technology Process of (R)-N-Benzylglutamic acid

There total 10 articles about (R)-N-Benzylglutamic 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: 73.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + benzaldehyde (100-52-7) → (S)-(+)-2-benzylamino glutaric acid (77539-18-5,73914-82-6)

Guidance literature:

L-glutamic acid; benzaldehyde; With triethylamine; In methanol; for 1h;

With sodium tetrahydroborate; In methanol; at 4 ℃; for 2h;

DOI:10.1021/jo035700b

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + benzaldehyde (100-52-7) → (R)-N-benzylglutamic acid (73914-82-6)

Guidance literature:

D-Glutamic acid; With water; sodium hydroxide; for 0.25h;

In ethanol; at 15 ℃; for 0.5h;

benzaldehyde; With sodium tetrahydroborate; In ethanol; at 0 - 15 ℃; for 3h;

Reference yield:

α-ketoglutaric acid (328-50-7) + benzylamine (100-46-9) → (S)-(+)-2-benzylamino glutaric acid (77539-18-5,73914-82-6) + (R)-N-benzylglutamic acid (73914-82-6)

Guidance literature:

With {Rh[(R,R)-Deguphos](COD)}BF₄; hydrogen; In methanol; dichloromethane; at 20 ℃; for 24h; under 45003.6 Torr; Title compound not separated from byproducts;

upstream raw materials:

Glutamic acid

L-glutamic acid

benzaldehyde

α-ketoglutaric acid

Downstream raw materials:

tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate

(2R-cis)-5-((1,1-Dimethylethoxy)carbonyl)-1-(phenylmethyl)-2-pyrrolidineacetic acid methyl ester

(2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester

(S)-N-benzyl-5-thioxoproline tert-butyl ester

Refernces

• 1、 -. "CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF". Paragraph 1637. . Retrieved 2018/04/17.
• 2、 Panday, Sharad Kumar,Pathak, Manoher Bhushan,Prasad, Jagdish. "An efficient and straight forward strategy for the synthesis of enantiomerically pure (S)-1-benzyl-5-(alkyl/aryl amino) methyl-pyrrolidin-2-ones". . p. 936 - 939. Retrieved 2015/08/06.