(4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid

Base Information

• Chemical Name: (4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid
• CAS No.: 207508-60-9
• Molecular Formula: C₁₃H₁₄F₃NO₄
• Molecular Weight: 305.254
• DSSTox Substance ID: DTXSID90435064
• Wikidata: Q82249747
• ChEMBL ID: CHEMBL351946
• Mol file: 207508-60-9.mol

Synonyms:(4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid;207508-60-9;(2S,4S)-2-Amino-4-(4-(trifluoromethyl)benzyl)pentanedioic acid;1233518-19-8;(2S,4S)-2-Amino-4-(4-trifluoromethyl-benzyl)-pentanedioic acid;(2S,4S)-2-amino-4-[[4-(trifluoromethyl)phenyl]methyl]pentanedioic acid;(2S,4S)-2-AMINO-4-{[4-(TRIFLUOROMETHYL)PHENYL]METHYL}PENTANEDIOIC ACID;CHEMBL351946;SCHEMBL2266372;DTXSID90435064;DGVMWWMTSDUMAQ-WPRPVWTQSA-N;MFCD07784142;AS-38505;CS-0170937;(2S,4S)-2-Amino-4-(4-(trifluoromethyl)benzyl)pentanedioicacid;(2s,4s)-2-amino-4-(4-trifluoromethylbenzyl)pentanedioic acid;(4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid, AldrichCPR

Chemical Property of (4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 305.08749241
• Heavy Atom Count: 21
• Complexity: 378

Purity/Quality:

98% ^*data from raw suppliers

(2S,4S)-2-Amino-4-(4-(trifluoromethyl)benzyl)pentanedioicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(CC(C(=O)O)N)C(=O)O)C(F)(F)F
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C[C@@H](C(=O)O)N)C(=O)O)C(F)(F)F

Technology Process of (4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid

There total 8 articles about (4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic 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: 90.0%

(2R,4S)-5-Oxo-4-(4-trifluoromethyl-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester → (2S,4R)-2-Amino-4-(4-trifluoromethyl-benzyl)-pentanedioic acid (207508-60-9)

Guidance literature:

(2R,4S)-5-Oxo-4-(4-trifluoromethyl-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester; With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 1h;

With methyloxirane; In methanol; at 20 ℃;

DOI:10.1021/jm020901d

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → (4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid (207508-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) lithium hexamethyldisilazide, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

2: MsCl, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

3: H₂ / PtO₂ / ethyl acetate / 4 h / 760 Torr / Ambient temperature

4: 6 N HCl / Heating

With hydrogenchloride; boron trifluoride diethyl etherate; hydrogen; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; platinum(IV) oxide; In dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(98)00091-2

Reference yield:

(S)-4-[Hydroxy-(4-trifluoromethyl-phenyl)-methyl]-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester → (4S)-4-(4-Trifluoromethyl-benzyl)-L-glutamic acid (207508-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: MsCl, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

2: H₂ / PtO₂ / ethyl acetate / 4 h / 760 Torr / Ambient temperature

3: 6 N HCl / Heating

With hydrogenchloride; hydrogen; methanesulfonyl chloride; triethylamine; platinum(IV) oxide; In dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(98)00091-2

upstream raw materials:

ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(p-trifluoromethyl)benzylpyroglutamate

4-Trifluoromethylbenzaldehyde

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Escribano, Ana,Ezquerra, Jesus,Pedregal, Concepcion,Rubio, Almudena,Yruretagoyena, Belen,Baker, S. Richard,Wright, Rebecca A.,Johnson, Bryan G.,Schoepp, Darryle D.. "(2S,3S)-2-Amino-3-(2,2-diphenylethyl)pentanedioic acid selective group 2 metabotropic glutamate receptor antagonist". . p. 765 - 770. Retrieved 2007/10/03.