Diethyl L-glutamate hydrochloride Chemical Properties

Melting point:

108-110 °C(lit.)

refractive index 

22.5 ° (C=3.6, EtOH)

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Soluble in water

form 

powder to crystal

color 

White to Almost white

optical activity

[α]18/D +22°, c = 1 in H2O

BRN 

3597595

InChI

InChI=1/C9H17NO4.ClH/c1-3-13-8(11)6-5-7(10)9(12)14-4-2;/h7H,3-6,10H2,1-2H3;1H/t7-;/s3

InChIKey

WSEQLMQNPBNMSL-WMASNCOMNA-N

SMILES

C(CC(=O)OCC)[C@H](N)C(=O)OCC.Cl |&1:7,r|

CAS DataBase Reference

1118-89-4(CAS DataBase Reference)

EPA Substance Registry System

L-Glutamic acid, diethyl ester, hydrochloride (1118-89-4)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

MA1252280

TSCA 

Yes

HS Code 

29224210

Toxicity

mouse,LD50,intraperitoneal,> 2gm/kg (2000mg/kg),Pharmaceutical Chemistry Journal Vol. 25, Pg. 246, 1991.

MSDS

• Language:English Provider:SigmaAldrich

Diethyl L-glutamate hydrochloride Usage And Synthesis

Chemical Properties

White crystal

Uses

L-Glutamic Acid Diethyl Ester Hydrochloride is a derivative of L-Glutamic Acid (G596960), a non-essential amino acid.

Uses

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.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

To a 500 mL four-necked round-bottomed flask equipped with a mechanical stirrer, a thermometer and a reflux condenser tube (connected to a 30% aqueous sodium hydroxide solution absorption system), 300 g of ethanol, 14.7 g (0.10 mol) of L-glutamic acid, and 25.0 g (0.08 mol) of triphosgene were added sequentially. The reaction mixture was heated to 70-75°C and maintained at this temperature with stirring for 5 hours. Upon completion of the reaction, the system was cooled to 20-25°C and the hydrogen chloride gas generated in the system was removed by nitrogen displacement, a process that lasted for 30 minutes. Subsequently, the excess triphosgene and ethanol were recovered by distillation. To the residue, 100 mL of methyl tert-butyl ether was added for pulping, and after filtration and drying, 23.5 g of the white solid product L-glutamic acid diethyl ester hydrochloride was obtained. The product was analyzed by liquid chromatography with 99.7% purity and 98.0% yield.

References

[1] Synthetic Communications, 2010, vol. 40, # 8, p. 1161 - 1179
[2] Patent: CN107602436, 2018, A. Location in patent: Paragraph 0051; 0052
[3] Patent: CN108218739, 2018, A. Location in patent: Paragraph 0116; 0117
[4] Chemistry of Natural Compounds, 1994, vol. 30, # 2, p. 238 - 244
[5] Khimiya Prirodnykh Soedinenii, 1994, # 2, p. 261 - 268

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