| Identification | More | [Name]
L-Glutamic acid di-tert-butyl ester hydrochloride | [CAS]
32677-01-3 | [Synonyms]
GLUTAMIC ACID DI-T-BUTYL ESTER HYDROCHLORIDE
GLUTAMIC ACID DI-TERT-BUTYL ESTER HYDROCHLORIDE
GLUTAMIC ACID(OTBU)-OTBU HCL
H-GLU(OBUT)-OBUT HCL
H-GLU(OTBU)-OTBU HCL
H-L-GLU(OTBU)-OTBU HCL
H-L-GLU(TBU)-OTBU HCL
L-GLUTAMIC ACID-ALPHA,GAMMA DI-T-BUTYL ESTER HYDROCHLORIDE
L-GLUTAMIC ACID ALPHA,GAMMA-DI-T-BUTYL ESTER HYDROCHLORIDE SALT
L-GLUTAMIC ACID DI-T-BUTYL ESTER HYDROCHLORIDE
L-GLUTAMIC ACID DI-TERT-BUTYL ESTER HYDROCHLORIDE
l-glutamicacid,bis(1,1-dimethylethyl)ester,hydrochloride
L-Glutamic Acid Di-tert-Butyl Ester HCl Salt
L-GLUTAMIC ACID DI-TERT-BUTYL ESTER HCL
H-Glu(OBut)-OBut
H-Glu(OtBu)-OtBu•
GLU(OTBU)-OTBU.HCL
L-GLUTAMIC ACID-A,Y DI-T-BUTYLESTER HYDROCHLORIDE | [Molecular Formula]
C13H26ClNO4 | [MDL Number]
MFCD00058003 | [Molecular Weight]
295.8 | [MOL File]
32677-01-3.mol |
| Hazard Information | Back Directory | [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]
H-Glu (OtBu)-OtBu hydrochloride can be used to synthesize PSMA probe 5, which was then labeled with 18F under Al catalysis for tumor imaging (radioactive probe [Al18F]5). [Al18F]5 (0.3-0.4 mCi; 1 hour after injection) shows PC3-PIP tumor uptake of 4.6% ID/g in PET imaging experiments, with a background as low as 0.04% ID/g[2]. | [References]
[1] Patent: US2004/87813, 2004, A1 |
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