L-Glutamic acid dimethyl ester hydrochloride Chemical Properties

Melting point:

89-90°C

alpha 

26 º (c=5% in H2O)

refractive index 

26 ° (C=5, H2O)

storage temp. 

2-8°C

solubility 

Methanol, Water

form 

Powder

color 

White

optical activity

[α]20/D +26.0±1°, c = 5% in H2O

Water Solubility 

Soluble in water, methanol (50 mg/ml).

Sensitive 

Hygroscopic

BRN 

4238829

Stability:

Hygroscopic

InChI

InChI=1/C7H13NO4.ClH/c1-11-6(9)4-3-5(8)7(10)12-2;/h5H,3-4,8H2,1-2H3;1H/t5-;/s3

InChIKey

MFUPLHQOVIUESQ-JEDNCBNOSA-N

SMILES

[C@@H](N)(C(=O)OC)CCC(=O)OC.Cl |&1:0,r|

CAS DataBase Reference

23150-65-4(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

L-Glutamic acid dimethyl ester hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Glutamic Acid Dimethyl Ester is a diester analogue of L-Glutamic Acid, a non-essential amino acid. L-Glutamic Acid Dimethyl Ester has been shown to antagonize the effects of morphine sulfate.

Uses

L-Glutamic acid dimethyl ester hydrochloride is used as a pharmaceutical intermediate.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

To a 500 mL four-necked flask equipped with a stirrer, thermometer and reflux condenser (connected to a 30% aqueous sodium hydroxide solution absorption unit), 300 g of methanol, 14.7 g (0.10 mol) of L-glutamic acid, and 30.0 g (0.25 mol) of thionyl chloride were added sequentially. The reaction mixture was heated to 60-63 °C and the reaction was stirred at this temperature for 7 hours. Upon completion of the reaction, the system was cooled to 20-25 °C, followed by the passage of nitrogen to displace the hydrogen chloride gas in the system for 30 min. Next, the excess thionyl chloride and methanol were recovered by distillation. To the residue, 100 g of methyl tert-butyl ether was added and pulped, followed by filtration to collect the solid. Upon drying, 20.8 g of L-glutamic acid dimethyl ester hydrochloride was obtained as a white solid. The product was analyzed by high performance liquid chromatography (HPLC) with 99.5% purity and 98.1% yield.

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 24, p. 6144 - 6153
[2] Archiv der Pharmazie, 2005, vol. 338, # 5-6, p. 281 - 290
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6273 - 6290
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 777 - 793
[5] Patent: CN107602436, 2018, A. Location in patent: Paragraph 0053; 0054

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