1118-89-4

Basic information

• Product Name: Diethyl L-glutamate hydrochloride
• Synonyms: diethylester,hydrochloride,l-glutamicaci;diethyll-glutaminatehydrochloride;L-GLUTAMIC ACID DIETHYL ESTER HYDROCHLORIDE;L-GLUTAMIC ACID ALPHA,GAMMA-DIESTER HYDROCHLORIDE;L-GLUTAMIC ACID ALPHA,GAMMA-DIETHYL ESTER HYDROCHLORIDE;GLUTAMIC ACID(OET)-OET HCL;H-GLU(OET)-OET HCL;DIETHYL L-GLUTAMATE HYDROCHLORIDE
• CAS NO: 1118-89-4
• Molecular Formula: C₉H₁₈NO₄*Cl
• Molecular Weight: 239.7
• EINECS: 214-270-4
• Product Categories: Glutamic acid [Glu, E];Amino Acids and Derivatives;Amino Acid Ethyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Glutamic AcidNeurotransmitters;Excitatory Amino Acids;Neurotransmitters;Amino Acid Derivatives;Glutamic Acid;Peptide Synthesis;peptides
• Mol File: 1118-89-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 108-110 °C(lit.)
• Boiling Point: 262 °C at 760 mmHg
• Flash Point: 86.3 °C
• Appearance: white crystalline powder
• Density: 1.08g/cm3
• Vapor Pressure: 0.0112mmHg at 25°C
• Refractive Index: 22.5 ° (C=3.6, EtOH)
• Storage Temp.: −20°C
• Water Solubility: Soluble in water
• BRN: 3597595
• CAS DataBase Reference: Diethyl L-glutamate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl L-glutamate hydrochloride(1118-89-4)
• EPA Substance Registry System: Diethyl L-glutamate hydrochloride(1118-89-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: MA1252280
• TSCA: Yes
• Hazardous Substances Data: 1118-89-4(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

Uses

Different sources of media describe the Uses of 1118-89-4 differently. You can refer to the following data:
1. L-Glutamic Acid Diethyl Ester Hydrochloride is a derivative of L-Glutamic Acid (G596960), a non-essential amino acid.
2. L-Glutamic acid diethyl ester hydrochloride can be used in the synthesis of:Oligo(γ-ethyl L-glutamate) via oligomerization catalyzed by papain.L-glutamic acid based dendritic compounds.Poly(α-peptide) by polymerization and copolymerization in the presence of protease catalysts.

InChI:InChI=1/C9H17NO4/c1-3-13-8(11)6-5-7(10)9(12)14-4-2/h7H,3-6,10H2,1-2H3

Synthetic route

L-glutamic acid (56-86-0) + acetyl chloride (75-36-5) → diethyl-L-glutamate hydrochloride (1118-89-4)

Conditions	Yield
In ethanol at 0℃; for 4h; Reflux;	99%

ethanol (64-17-5) + L-glutamic acid (56-86-0) → diethyl-L-glutamate hydrochloride (1118-89-4)

Conditions	Yield
With thionyl chloride	98%
Stage #1: ethanol; L-glutamic acid With bis(trichloromethyl) carbonate at 70 - 75℃; for 5h; Stage #2: With hydrogenchloride at 20 - 25℃; for 0.5h;	98%
Stage #1: ethanol With thionyl chloride at -10 - 10℃; for 1h; Stage #2: L-glutamic acid at 20 - 80℃; for 2h;	77.76%

L-glutamic acid (56-86-0) → diethyl-L-glutamate hydrochloride (1118-89-4)

Conditions	Yield
at 190 - 195℃; unter vermindertem Druck, Kochen der gebildeten (S)-5-Oxo-pyrrolidin-carbonsaeure-(2) mit aethanol.HCl;

ethanol (64-17-5) + (S)-2-Amino-pentanedioic acid 5-ethyl ester (1119-33-1) → diethyl-L-glutamate hydrochloride (1118-89-4)

Conditions	Yield
With thionyl chloride at 20℃; for 25h; Cooling with ice;

diethyl-L-glutamate hydrochloride (1118-89-4) + 2,5-difluoro-4-nitrobenzoyl chloride → diethyl N-(2,5-difluoro-4-nitrobenzoyl)-L-glutamate (7498-31-9)

Conditions	Yield
With triethylamine In dichloromethane for 1h;	100%

diethyl-L-glutamate hydrochloride (1118-89-4) + (4-Chlorocarbonyl-3,5-difluoro-phenyl)-prop-2-ynyl-carbamic acid tert-butyl ester → diethyl N-(4-(N-(tert-butyloxycarbonyl)-N-prop-2-ynylamino)-2,6-difluorobenzoyl)-L-glutamate (141412-75-1)

Conditions	Yield
With triethylamine In dichloromethane for 2h;	100%

diethyl-L-glutamate hydrochloride (1118-89-4) + 4-(2-amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-benzoic acid → diethyl N-{4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]benzoyl}-L-glutamate (150585-92-5)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	100%

5-bromo-3-methyl-thiophene-2-carboxylic acid (38239-45-1) + diethyl-L-glutamate hydrochloride (1118-89-4) → 2(S)-{[(5-bromo-3-methylthiophene-2-yl)carbonyl]amino}pentanedioic acid diethyl ester (160743-92-0)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 18h;	99%

monomethyl oxalyl chloride (5781-53-3) + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-2-(methoxyoxalyl-amino)pentanedioic acid diethyl ester

Conditions	Yield
In toluene	99%

diethyl-L-glutamate hydrochloride (1118-89-4) + 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline (404586-94-3) → diethyl (tert-butoxycarbonyl)-L-glutamate (130696-54-7)

Conditions	Yield
In diethyl ether Heating;	98%

Boc-Lys(Z)-OH (2389-45-9) + diethyl-L-glutamate hydrochloride (1118-89-4) → Boc-Lys(Cbz)-Glu(Et)-OEt (138680-20-3)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; Alkaline conditions;	98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 16h;	77%

diethyl-L-glutamate hydrochloride (1118-89-4) → L-glutamic acid diethyl ester (16450-41-2)

Conditions	Yield
With potassium carbonate In water for 0.5h;	97.5%
With Amberlyst A21 resin In dichloromethane at 0 - 20℃; for 2h;	94%
With ammonia In diethyl ether; water at 20℃; for 2h;

diethyl-L-glutamate hydrochloride (1118-89-4) + C64H36N4O8(2-)*Pd(2+) → C100H96N8O20(2-)*Pd(2+)

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;	96%

diethyl-L-glutamate hydrochloride (1118-89-4) + 5-{[(2-Fluoro-ethyl)-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-amino]-methyl}-thiophene-2-carboxylic acid (133446-79-4) → (S)-2-[(5-{[(2-Fluoro-ethyl)-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-amino]-methyl}-thiophene-2-carbonyl)-amino]-pentanedioic acid diethyl ester (133447-08-2)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;	95%

diethyl-L-glutamate hydrochloride (1118-89-4) + 3,4-dimethoxy-3-cyclobutene-1,2-dione (5222-73-1) → (S)-diethyl 2-((2-methoxy-3,4-dioxocyclobut-1-en-1-yl)amino)pentanedioate

Conditions	Yield
With triethylamine In methanol at 20℃; for 24h;	95%

diethyl-L-glutamate hydrochloride (1118-89-4) + 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid (137281-39-1) → N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester (146943-43-3)

Conditions	Yield
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; sodium hydroxide In ethanol; water at 40℃; for 3h;	94.5%
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine at 20℃; Condensation;	62%
Stage #1: 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: diethyl-L-glutamate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 3.5h;	62%
With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; 4-methylmorpholine N-oxide In N,N-dimethyl-formamide at 25℃; for 1.5h; Large scale;
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 6h;

phosgene (75-44-5) + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-(-)-2-isocyanatoglutaric acid diethyl ester (145080-95-1)

Conditions	Yield
With pyridine In tetrahydrofuran; dichloromethane at 0℃; for 2h;	94%

diethyl-L-glutamate hydrochloride (1118-89-4) + benzyl chloride (100-44-7) + methyl chloroacetate (96-34-4) → N-methoxycarbonylmethyl-N-benzyl-L-glutamic acid diethyl ester

Conditions	Yield
Stage #1: diethyl-L-glutamate hydrochloride; methyl chloroacetate With potassium carbonate; potassium iodide In acetonitrile at 20 - 80℃; Stage #2: benzyl chloride In acetonitrile at 80℃;	93.5%

diethyl-L-glutamate hydrochloride (1118-89-4) + 1-bromomethyl-4-nitro-benzene (100-11-8) → diethyl N-(p-nitrobenzyl)-L-glutamate (83314-83-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 72h; Ambient temperature;	92%

diethyl-L-glutamate hydrochloride (1118-89-4) + 5-Nitroindole-2-carbonyl chloride (103868-02-6) → Diethyl L-glutamate (109707-70-2)

Conditions	Yield
With triethylamine In chloroform; ethyl acetate at 20℃; for 0.5h;	91.9%

2-[9,10-dioxo-4-(p-tolylamino)-9,10-dihydroanthracen-1-oxyl]acetic acid + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-diethyl 2-{2-[9,10-dioxo-4-(p-tolylamino)-9,10-dihydroanthracen-1-oxyl]acetamido}pentanedioate

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	91.9%

3-(N-ethyl-N-{4'-[(4''-nitrophenyl)azo]phenyl}amino)propanoic acid (81338-13-8) + diethyl-L-glutamate hydrochloride (1118-89-4) → C26H33N5O7 (1174937-08-6)

Conditions	Yield
Stage #1: 3-(N-ethyl-N-{4'-[(4''-nitrophenyl)azo]phenyl}amino)propanoic acid With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With chloroformic acid ethyl ester In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: diethyl-L-glutamate hydrochloride With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	91%

4-bromo-thiophene-2-carboxylic acid (16694-18-1) + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-2-[(4-bromothiophene-2-carbonyl)amino]pentanedioic acid diethyl ester (1286279-56-8)

Conditions	Yield
Stage #1: 4-bromo-thiophene-2-carboxylic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: diethyl-L-glutamate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 12h;	91%

3-bromothiophene-2-carboxylic acid (7311-64-0) + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-2-[(3-bromothiophene-2-carbonyl)amino]pentanedioic acid diethyl ester (1286279-52-4)

Conditions	Yield
Stage #1: 3-bromothiophene-2-carboxylic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: diethyl-L-glutamate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 12h;	91%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + diethyl-L-glutamate hydrochloride (1118-89-4) → (2S)-(-)-diethyl-2-(pyrrol-1-yl)-pentanedioate (157034-04-3)

Conditions	Yield
In water; 1,2-dichloro-ethane at 80℃; for 2h;	90%
In water; 1,2-dichloro-ethane at 80℃; for 0.75h;	81%
In water; 1,2-dichloro-ethane at 80℃; for 0.75h;	81%
In water; 1,2-dichloro-ethane at 80℃; for 0.833333h;	80%
In water at 80℃; for 0.5h;	62%

diethyl-L-glutamate hydrochloride (1118-89-4) + 5-[(2-Methyl-4-oxo-3,4-dihydro-quinazolin-6-ylamino)-methyl]-pyridine-2-carboxylic acid → (S)-2-({5-[(2-Methyl-4-oxo-3,4-dihydro-quinazolin-6-ylamino)-methyl]-pyridine-2-carbonyl}-amino)-pentanedioic acid diethyl ester (133447-11-7)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;	90%

di-tert-butyl dicarbonate (24424-99-5) + diethyl-L-glutamate hydrochloride (1118-89-4) → diethyl (tert-butoxycarbonyl)-L-glutamate (130696-54-7)

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 0 - 55℃; for 15.25h;	90%
With triethylamine at 20℃; for 48h; Acylation;	34%
With triethylamine; dmap In acetonitrile at 20℃;

diethyl-L-glutamate hydrochloride (1118-89-4) + chloro-diphenylphosphine (1079-66-9) → (S)-N-diphenylphosphinoglutamic acid diethyl ester (368879-75-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 5℃; for 3h;	90%
With triethylamine

diethyl-L-glutamate hydrochloride (1118-89-4) + C22H26N4O5 → (R,S)-N-[4-[1-ethyl-2-(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester (425663-99-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 6h;	90%

2-{p-[2'-methoxy-4'-(p-nitrophenylazo)phenylazo]phenoxy}-acetic acid (1174937-13-3) + diethyl-L-glutamate hydrochloride (1118-89-4) → N-(2-{4-[2'-methoxy-4'-(p-nitrophenylazo)phenylazo]phenoxy}-acetyl)-glutamic acid diethyl ester (1174937-14-4)

Conditions	Yield
Stage #1: 2-{p-[2'-methoxy-4'-(p-nitrophenylazo)phenylazo]phenoxy}-acetic acid With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With chloroformic acid ethyl ester In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: diethyl-L-glutamate hydrochloride With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	90%

2-bromothiophene-4-carboxylic acid (100523-84-0) + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-2-[(5-bromothiophene-3-carbonyl)amino]pentanedioic acid diethyl ester (1286279-58-0)

Conditions	Yield
Stage #1: 2-bromothiophene-4-carboxylic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: diethyl-L-glutamate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 12h;	90%

2-bromothiophene-3-carboxylic acid (24287-95-4) + diethyl-L-glutamate hydrochloride (1118-89-4) → (S)-2-[(2-bromothiophene-3-carbonyl)amino]pentanedioic acid diethyl ester (1286279-50-2)

Conditions	Yield
Stage #1: 2-bromothiophene-3-carboxylic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: diethyl-L-glutamate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 12h;	90%

Upstream product

• 64-17-5 ethanol 
• 56-86-0 L-glutamic acid 
• 1119-33-1 (S)-2-Amino-pentanedioic acid 5-ethyl ester 
• 75-36-5 acetyl chloride 

Downstream Products

• 21612-21-5 (S)-2-(3-Benzyloxycarbonylamino-propionylamino)-pentanedioic acid diethyl ester 
• 3369-03-7 N-(N-benzyloxycarbonyl-glycyl)-L-glutamic acid diethyl ester 
• 133446-60-3 diethyl N-[(4-chloromethyl)benzoyl]-L-glutamate 
• 116387-23-6 diethyl N-(4-ethynylbenzoyl)-L-glutamate 
• 106585-55-1 diethyl N-(2-fluoro-4-nitrobenzoyl)-L-glutamate 
• 56277-36-2 diethyl 4-formylbenzoyl-L-glutamate 
• 65148-67-6 N_.N'-(N-benzyloxycarbonyl-L-glutamoyl)-bis-L-glutamic acid tetraethyl ester 
• 476374-15-9 (S)-2-{2-[4-(6,7-Difluoro-quinoxalin-2-ylamino)-phenyl]-acetylamino}-pentanedioic acid diethyl ester 
• 476374-16-0 (S)-2-{2-[4-(3-Carboxy-quinoxalin-2-ylamino)-phenyl]-acetylamino}-pentanedioic acid diethyl ester 
• 476374-14-8 (S)-2-{2-[4-(3-Thiophen-2-yl-quinoxalin-2-ylamino)-phenyl]-acetylamino}-pentanedioic acid diethyl ester 
• 476374-13-7 (S)-2-{2-[4-(3-Phenyl-quinoxalin-2-ylamino)-phenyl]-acetylamino}-pentanedioic acid diethyl ester 
• 476374-18-2 (S)-2-{2-[4-(3-Carboxy-6,7-difluoro-quinoxalin-2-ylamino)-phenyl]-acetylamino}-pentanedioic acid diethyl ester 
• 528597-19-5 diethyl N-[4-[2-(2-amino-4-oxopyrido[3,4-d]pyrimidin-6-yl)ethyl]-benzoyl]-L-glutamate 
• 528597-31-1 diethyl N-[4-[2-(2,4-diaminopyrido[3,4-d]pyrimidin-6-yl)ethyl]benzoyl]-L-glutamate 

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