1676-73-9

Basic information

• Product Name: gamma-Benzyl L-glutamate
• Synonyms: GLUTAMIC ACID(OBZL)-OH;GLUTAMIC ACID-GAMMA-BENZYL ESTER;H-L-GLU(OBZL)-OH;H-L-GLU(BZL)-OH;H-GLU(OBZL)-OH;GLU(OBZL);GAMMA-BENZYL-L-GLUTAMATE;GAMA-BENZYL L-GLUTAMATE
• CAS NO: 1676-73-9
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• EINECS: 216-826-1
• Product Categories: Amino Acids Derivatives;AMINOACIDS DERIVATIVES;API intermediates;Amino Acids;Glutamic acid [Glu, E];Amino Acids and Derivatives;amino acid
• Mol File: 1676-73-9.mol
• Article Data: 46

Chemical Properties

• Melting Point: 181-182 °C(lit.)
• Boiling Point: 379.78°C (rough estimate)
• Flash Point: 211.5 °C
• Appearance: White/Powder
• Density: 1.2026 (rough estimate)
• Vapor Pressure: 9.12E-09mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Acetic Acid (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 2.20±0.10(Predicted)
• BRN: 1885646
• CAS DataBase Reference: gamma-Benzyl L-glutamate(CAS DataBase Reference)
• NIST Chemistry Reference: gamma-Benzyl L-glutamate(1676-73-9)
• EPA Substance Registry System: gamma-Benzyl L-glutamate(1676-73-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1676-73-9(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

L-Glutamic acid γ-benzyl ester is commonly used in the synthesis of polymers for biological applications. Some of the examples are:Synthesis of bioreducible block copolymers based on poly(ethylene glycol) and poly(γ-benzyl L-glutamate) for Intracellular drug delivery.Synthesis of biodegradable poly(L-glutamic acid)-b-polylactide for magnetic resonance imaging (MRI)-visible drug delivery system.Synthesis of pH and temperature-responsive diblock copolymers based on poly(L-glutamic acid).

Purification Methods

Recrystallise the ester from H2O and store it at 0o. [Estrin Biochemical Preparations 13 25 1971, Beilstein 6 IV 2538.]

InChI:InChI=1/C12H15NO4/c13-10(12(16)17)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,13H2,(H,14,15)(H,16,17)/p-1/t9-,10+/m1/s1

Synthetic route

Z(OMe)-Glu(OBzl)-OH (23506-06-1) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With methanesulfonic acid; 3-methyl-phenol In dichloromethane at 25℃; for 0.5h;	100%

L-glutamic acid (56-86-0) + benzyl alcohol (100-51-6) → L-glutamic acid γ-benzyl ester (1676-73-9) + 1-benzyl L-glutamate (13030-09-6)

Conditions	Yield
With copper dichloride at 60℃; for 2h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Temperature;	A 95.31% B n/a

L-glutamic acid (56-86-0) + benzyl alcohol (100-51-6) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With tetrafluoroboric acid diethyl ether; sodium sulfate for 15h; Ambient temperature;	94%
With tetrafluoroboric acid diethyl ether; sodium sulfate at 20℃; for 12h; Inert atmosphere;	80%
Stage #1: L-glutamic acid; benzyl alcohol With methanesulfonic acid In toluene at 30 - 45℃; for 6h; Stage #2: With ammonia In ethanol; water at 60℃; for 2h; pH=6.5 - 7;	77%

dibenzyl L-glutamate (2768-50-5) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With water In acetone at 37℃; for 4h; Alcalase, pH 8.2;	85%
In ethanol; water at 25℃; for 3h; pronase (E C 3.4.24.4.), pH 7.2;	72%
(i) TsOH, (ii) CuSO4*5H2O, aq. NaOH, EtOH, Na2H2edta; Multistep reaction;

Copper(II); (S)-2-amino-4-benzyloxycarbonyl-butyrate → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With sodium sulfide In water at 25 - 30℃; for 0.166667h;	84%

γ-benzyl L-glutamate methanesulphonate → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With ammonia In water at 13 - 15℃; for 2h; pH=5.9 - 6.3;	81%

L-glutamic acid (56-86-0) + benzyl bromide (100-39-0) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With copper	70%
Yield given. Multistep reaction;

Oδ-Bzl-L-Glu/copper complex → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With N,N-Dibutyl-N'-(benzoyl)thioharnstoff In ethanol for 2h; Heating;	60%

L-glutamic acid (56-86-0) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
at 120℃; under 2 Torr;

L-glutamic acid (56-86-0) + benzenesulfonic acid (98-11-3) + benzyl alcohol (100-51-6) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
at 100 - 105℃;

benzyl bromide (100-39-0) + 3-((S)-2,2-Diethyl-5-oxo-4,5-dihydro-3λ5,2λ5-[1,3,2]oxazaborol-4-yl)-propionic acid → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With hydrogenchloride; N-cyclohexyl-cyclohexanamine 1) DMF, 60-70 degC, 5 min; 2) EtOAc; Yield given. Multistep reaction;

iodomethylbenzene (620-05-3) + 2C5H7NO4(2-)*Cu(2+)*2Na(1+) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
In water; N,N-dimethyl-formamide

L-glutamic acid dibenzyl ester 4-toluenesulfonate (2791-84-6) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With ethylenediaminetetraacetic acid; water; copper(II) sulfate 1.) EtOH, 32 deg C, 60 min, 2.) EtOH, 100 deg C; Yield given; Multistep reaction;

L-glutamic acid (56-86-0) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / benzene / Heating 2: 1.) CuSO4*5H2O, H2O, 2.) EDTA, H2O / 1.) EtOH, 32 deg C, 60 min, 2.) EtOH, 100 deg C View Scheme

toluene-4-sulfonic acid (104-15-4) + 4-polystyryltriphenylmethyl-Phe-ODpm → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / benzene / Heating 2: 1.) CuSO4*5H2O, H2O, 2.) EDTA, H2O / 1.) EtOH, 32 deg C, 60 min, 2.) EtOH, 100 deg C View Scheme

D-Glutamic acid (6893-26-1) + benzyl alcohol (100-51-6) → L-glutamic acid γ-benzyl ester (1676-73-9)

Conditions	Yield
With sulfuric acid at 70℃;

L-glutamic acid γ-benzyl ester (1676-73-9) + di-tert-butyl dicarbonate (24424-99-5) → Boc-Glu(OBzl)-OH (13574-13-5)

Conditions	Yield
In 1,4-dioxane; water at 0℃;	100%
In 1,4-dioxane; water at 0℃;	100%
With triethylamine In N,N-dimethyl-formamide at 60℃; for 0.5h;	98%

L-glutamic acid γ-benzyl ester (1676-73-9) → L-glutamic acid (56-86-0)

Conditions	Yield
With dimethylsulfide; hydrogen fluoride; methoxybenzene at 0℃; for 1h; Product distribution; Rate constant; other concentration of reagents;	100%
With dimethylsulfide; trifluorormethanesulfonic acid; 30 (v/v); trifluoroacetic acid at 0℃; for 4h; Yield given;
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.0333333h; pH=10.5; aq. buffer; Enzymatic reaction;
With E. coli BL21 Star (DE3) S30 extract In aq. buffer at 37℃; for 6h; pH=7.5;

L-glutamic acid γ-benzyl ester (1676-73-9) + Boc-Ala-O-N-hydroxysuccinimide (3392-05-0) → Boc-Ala-Glu(OBzl)-OH (17080-23-8)

Conditions	Yield
With 4-methyl-morpholine In 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine; water at 20℃; for 12 - 18h; pH=~ 9 - 9.2;	100%
With potassium hydrogencarbonate In tetrahydrofuran; water at 20℃;
With 4-methyl-morpholine In 1,4-dioxane; water at 20℃; for 12h;

L-glutamic acid γ-benzyl ester (1676-73-9) + 2,5-dioxopyrrolidin-1-yl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysinate (132307-50-7) → Fmoc-L-Lys(Boc)-L-Glu(OBzl)-OH (1006066-87-0)

Conditions	Yield
With 4-methyl-morpholine In 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine; water at 20℃; for 12 - 18h; pH=~ 9 - 9.2;	100%

Boc-Leu-ONSu (3392-09-4) + L-glutamic acid γ-benzyl ester (1676-73-9) → Boc-Leu-Glu(OBzl)-OH (32945-71-4)

Conditions	Yield
With 4-methyl-morpholine In 1,4-dioxane; water at 20℃; for 12h;	100%
With potassium hydrogencarbonate In tetrahydrofuran; water at 20℃;

L-glutamic acid γ-benzyl ester (1676-73-9) + N-ethoxycarbonylphthalimide (22509-74-6) → (2S)-4-benzyloxicarbonyl-2-phthalimidobutanoic acid (88784-33-2)

Conditions	Yield
With TEA In tetrahydrofuran Heating;	98%
With sodium carbonate

L-glutamic acid γ-benzyl ester (1676-73-9) → benzyl-3-(3H-diazirin-3-yl)propanoate

Conditions	Yield
With [bis(acetoxy)iodo]benzene; ammonia In methanol at 0 - 20℃; for 2h; Inert atmosphere;	98%

polystyrene-NHCH2CH2N(CH2CH2NH2)2, Mn = 2180, Mw/Mn = 1.15 + L-glutamic acid γ-benzyl ester (1676-73-9) → (polystyrene)25-NHCH2CH2N(CH2CH2NH-(γ-benzyl-L-glutamate)51)2, Mn = 7460, Mw/Mn = 1.26

Conditions	Yield
In dichloromethane at 20℃; for 24h;	97%

phosgene (75-44-5) + L-glutamic acid γ-benzyl ester (1676-73-9) → 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4)

Conditions	Yield
In tetrahydrofuran; toluene at 50℃; for 1h;	95.4%
In tetrahydrofuran; toluene at 50℃; for 1.16h;	95.4%
In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;	93.5%

bis(trichloromethyl) carbonate (32315-10-9) + L-glutamic acid γ-benzyl ester (1676-73-9) → 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4)

Conditions	Yield
In tetrahydrofuran at 40℃; Inert atmosphere;	95.1%
at 50℃; for 12h; Inert atmosphere;	94%
In ethyl acetate for 3h; Inert atmosphere; Reflux;	92%

L-glutamic acid γ-benzyl ester (1676-73-9) + trichloromethyl chloroformate (503-38-8) → 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; ethanol; water for 1.5h; Inert atmosphere; Reflux;	95%
In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;	95%
In tetrahydrofuran at 70℃; Inert atmosphere;	95%

Cbz-Gly-ONSuc (2899-60-7) + L-glutamic acid γ-benzyl ester (1676-73-9) → Z-Gly-Glu(OBzl)-OH (100736-69-4)

Conditions	Yield
With calcium(II) nitrate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Condensation;	94%

L-glutamic acid γ-benzyl ester (1676-73-9) + (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (769922-77-2) → Cbz-L-Phe-L-Glu(OBn)-OH (14297-16-6)

Conditions	Yield
With triethylamine In water; acetonitrile	93%

L-glutamic acid γ-benzyl ester (1676-73-9) + 1-O-benzyl 4-O-(2,-5-dioxopyrrolidin-1-yl) butanedioate (117679-91-1) → N-benzylsuccinyl-γ-benzyl-glutamic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	93%

methanol (67-56-1) + L-glutamic acid γ-benzyl ester (1676-73-9) → L-glutamic acid α-methyl γ-benzyl diester hydrochloride (41089-47-8)

Conditions	Yield
With thionyl chloride at 0 - 22℃;	92%

Boc-Val-ONSu (3392-12-9) + L-glutamic acid γ-benzyl ester (1676-73-9) → Boc-Val-Glu(OBzl)-OH

Conditions	Yield
With 4-methyl-morpholine In 1,4-dioxane; water at 20℃; for 12h;	92%

L-glutamic acid γ-benzyl ester (1676-73-9) + benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate (820239-42-7) → Cbz-L-Ala-L-Glu(OBn)-OH

Conditions	Yield
With triethylamine In water; acetonitrile	91%

bis(trichloromethyl) carbonate (32315-10-9) + L-glutamic acid γ-benzyl ester (1676-73-9) → C12H14ClNO3

Conditions	Yield
In tetrahydrofuran at 60℃; for 3h;	90%

L-glutamic acid γ-benzyl ester (1676-73-9) → 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4)

Conditions	Yield
With phosgene In tetrahydrofuran at 45 - 65℃; for 1.08333h;	89.2%
With phosgene In tetrahydrofuran; toluene for 8h; Ambient temperature;	88.3%
Multi-step reaction with 2 steps 1: aqueous KHCO3 2: PCl5 View Scheme
With bis(trichloromethyl) carbonate; α-pinene In ethyl acetate at 105℃;
With bis(trichloromethyl) carbonate

L-glutamic acid γ-benzyl ester (1676-73-9) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h;	88.3%

L-glutamic acid γ-benzyl ester (1676-73-9) + benzyl chloroformate (501-53-1) → N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid (5680-86-4)

Conditions	Yield
With sodium hydrogencarbonate for 18h; Ambient temperature;	88%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1h;	86%
With potassium hydrogencarbonate
With potassium carbonate
With sodium hydrogencarbonate In diethyl ether

bis(trichloromethyl) carbonate (32315-10-9) + L-glutamic acid γ-benzyl ester (1676-73-9) → 3-(2,5-dioxo-oxazolidin-4-yl)-propionic acid benzyl ester (5254-51-3, 3190-71-4, 10289-08-4, 13822-45-2)

Conditions	Yield
In tetrahydrofuran at 65℃; for 2h;	87.6%
In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;	49%
In tetrahydrofuran at 45℃; for 3h;

sarcosine-N-carboxyanhydride (5840-76-6) + 2,2-dimethylpropylamine (5813-64-9) + D-glutamic acid benzyl ester-N-carboxylic anhydride + L-glutamic acid γ-benzyl ester (1676-73-9) → Sar125-b-p-[D-Glu(OBn)15-co-L-Glu(OBn)15]

Conditions	Yield
Stage #1: sarcosine-N-carboxyanhydride; 2.2-dimethylpropylamine In N,N-dimethyl-formamide for 20h; Darkness; Stage #2: D-glutamic acid benzyl ester-N-carboxylic anhydride; L-glutamic acid γ-benzyl ester In N,N-dimethyl-formamide at 25℃; for 24h;	86%

sarcosine-N-carboxyanhydride (5840-76-6) + 2,2-dimethylpropylamine (5813-64-9) + D-glutamic acid benzyl ester-N-carboxylic anhydride + L-glutamic acid γ-benzyl ester (1676-73-9) → Sar175-b-p-[D-Glu(OBn)25-co-L-Glu(OBn)25]

Conditions	Yield
Stage #1: sarcosine-N-carboxyanhydride; 2.2-dimethylpropylamine In N,N-dimethyl-formamide for 20h; Darkness; Stage #2: D-glutamic acid benzyl ester-N-carboxylic anhydride; L-glutamic acid γ-benzyl ester In N,N-dimethyl-formamide at 25℃; for 24h;	86%

sarcosine-N-carboxyanhydride (5840-76-6) + 2,2-dimethylpropylamine (5813-64-9) + D-glutamic acid benzyl ester-N-carboxylic anhydride + L-glutamic acid γ-benzyl ester (1676-73-9) → Sar175-b-p-[D-Glu(OBn)25-co-L-Glu(OBn)25]

Conditions	Yield
Stage #1: sarcosine-N-carboxyanhydride; 2.2-dimethylpropylamine In water; N,N-dimethyl-formamide; isopropyl alcohol for 20h; Darkness; Stage #2: D-glutamic acid benzyl ester-N-carboxylic anhydride; L-glutamic acid γ-benzyl ester In N,N-dimethyl-formamide at 25℃; for 24h;	86%

phosgene (75-44-5) + L-glutamic acid γ-benzyl ester (1676-73-9) → γ-benzyl L-glutamate N-carboxyanhydride

Conditions	Yield
In tetrahydrofuran at 45 - 48℃; for 4h;	84.7%

Upstream product

• 56-86-0 L-glutamic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 
• 98-11-3 benzenesulfonic acid 
• 2791-84-6 L-glutamic acid dibenzyl ester 4-toluenesulfonate 
• 6893-26-1 D-Glutamic acid 
• 620-05-3 iodomethylbenzene 
• 100-39-0 benzyl bromide 
• 23506-06-1 Z(OMe)-Glu(OBzl)-OH 
• 2768-50-5 dibenzyl L-glutamate 

Downstream Products

• 5680-86-4 N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid 
• 59486-73-6 (2R)-5-(benzyloxy)-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 80165-23-7 (S)-2-aminopentanedioic acid 5-benzyl ester 1-tert-butyl ester 
• 88784-33-2 (2S)-4-benzyloxicarbonyl-2-phthalimidobutanoic acid 
• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 7536-59-6 Boc-Glu(OBzl)-ONp 
• 192123-42-5 (S)-2-(6-Benzylsulfanyl-hexylamino)-pentanedioic acid 5-benzyl ester 
• 3190-71-4 5-benzyl L-glutamate N-carboxyanhydride 
• 100736-69-4 Z-Gly-Glu(OBzl)-OH 
• 104091-11-4 N-Fmoc-D-Glu γ-benzyl ester 
• 306776-74-9 α-bromoglutaric acid 1-tert-butyl ester 5-benzyl ester 
• 41089-47-8 L-glutamic acid α-methyl γ-benzyl diester hydrochloride 
• 263247-61-6 (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N_α-t-butoxycarbonylglutamic acid amide 

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