L-Glutamic acid di-tert-butyl ester hydrochloride Chemical Properties

Melting point:

133-135 °C

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in methanol (50gmg/ml).

form 

Solid

color 

White to Off-White

BRN 

3573738

CAS DataBase Reference

32677-01-3(CAS DataBase Reference)

Safety Information

WGK Germany 

3

RTECS 

MA0880000

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

L-Glutamic acid di-tert-butyl ester hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Glutamic acid di-tert-butyl ester may be useful in the synthesis of substance P antagonistic peptides.

Biological Activity

Glutamic acid di-tert butyl ester (GTBE) possesses convulsant properties in mice and rats. It might have unique pharmacological features th at set it apart from other convulsant medications.', 'L-Glutamic acid di-tert-butyl ester is C-terminal and R-chain blocked derivative of L-glutamate th at may be useful in the synthesis of substance P antagonistic peptides.

Synthesis

Example 5 Synthesis of L-glutamic acid di-tert-butyl ester hydrochloride (15A): L-glutamic acid (14) (4.4 g, 30 mmol) was suspended in chloroform (120 mL) and concentrated sulfuric acid (3 mL, 56 mmol) was added. The suspension was cooled to -78 °C, followed by the slow addition of liquefied isobutene (70 mL). The reaction mixture was gradually warmed to room temperature with stirring and the reaction was continued for 18 hours. Upon completion of the reaction, the suspended solids were completely dissolved to form a clarified solution. The solution was bubbled with nitrogen gas for 10 min to remove the residual isobutene, followed by washing with saturated aqueous NaHCO3 solution (2 x 100 mL) and distilled water (100 mL) in that order. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to remove the solvent. The crude product was placed in a desiccator and dried in the presence of NaOH particles for 48 h to give L-glutamic acid di-tert-butyl ester (15) (6.7 g, 86% yield) as an oil.1H-NMR (δH): 1.39 (s, 9H, COO-t-Bu), 1.41 (s, 9H, COO-t-Bu), 1.60-1.90 (m, 2H CH2CH(NH2)-), 2.15-2.35 (m, 2H, CH2COO), 2.85 (s, 2H, NH2), 3.20-3.35 (m, 1H, CH(NH2)-).MS (ESI): m/z 260 ([M+H]+, 100%), 283 ([M+Na]+, 10%).

in vivo

References

[1] Patent: US2004/87813, 2004, A1

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