| Identification | More | [Name]
Diethyl L-glutamate hydrochloride | [CAS]
1118-89-4 | [Synonyms]
DIETHYL L-GLUTAMATE HYDROCHLORIDE
GLUTAMIC ACID(OET)-OET HCL
H-GLU(OET)-OET HCL
L-GLUTAMIC ACID ALPHA,GAMMA-DIESTER HYDROCHLORIDE
L-GLUTAMIC ACID ALPHA,GAMMA-DIETHYL ESTER HYDROCHLORIDE
L-GLUTAMIC ACID DIETHYL ESTER HYDROCHLORIDE
diethylester,hydrochloride,l-glutamicaci
diethyll-glutaminatehydrochloride
L-Glutamic Acid Diethyl Ester HCl
GLUTAMICACID,DIETHYLESTERHYDROCHLORIDE
L-GLUTAMATE DIETHYL ESTER
L-GLUTAMIC ACID A,Y-DIETHYLESTER HYDROCHLORIDE | [EINECS(EC#)]
214-270-4 | [Molecular Formula]
C9H18ClNO4 | [MDL Number]
MFCD00012509 | [Molecular Weight]
239.7 | [MOL File]
1118-89-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
108-110 °C(lit.)
| [refractive index ]
22.5 ° (C=3.6, EtOH) | [storage temp. ]
−20°C
| [Water Solubility ]
Soluble in water | [form ]
powder to crystal | [color ]
White to Almost white | [Optical Rotation]
[α]18/D +22°, c = 1 in H2O | [BRN ]
3597595 | [Major Application]
peptide synthesis | [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]
1118-89-4(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
3
| [RTECS ]
MA1252280
| [TSCA ]
Yes | [HS Code ]
29224210 | [Storage Class]
11 - Combustible Solids | [Toxicity]
mouse,LD50,intraperitoneal,> 2gm/kg (2000mg/kg),Pharmaceutical Chemistry Journal Vol. 25, Pg. 246, 1991. |
| Hazard Information | Back Directory | [Chemical Properties]
White crystal | [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.
| [Uses]
L-Glutamic Acid Diethyl Ester Hydrochloride is a derivative of L-Glutamic Acid (G596960), a non-essential amino acid. | [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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